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303-45-7

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  • [2,2'-Binaphthalene]-8,8'-dicarboxaldehyde,1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)- 303-45-7

    Cas No: 303-45-7

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303-45-7 Usage

Description

Gossypol is mainly present in the roots, stems, leaves, and seeds of the plant cotton, and the highest content is found in cotton seeds. Its chemical structure was first determined by Adams in 1938 and was used to be studied in antitumor research.

Chemical Properties

Soild

Physical properties

Appearance: plate or needle-like crystals with yellow color, odorless, and tasteless. Solubility: do not dissolve in water, slightly soluble in ethanol, and soluble in chloroform, ether, acetone, ethyl acetate, dichloroethane, carbon tetrachloride, and pyridine. Difficult to dissolve in cyclohexane, benzene, and petroleum ether. Melting point: 184–214?°C. Gossypol has a chiral structure with two optical isomers in the left and right. The formic acid gossypol or gossypol acetate was commonly used.

Occurrence

Gossypol is found in cotton and is made synthetically.

History

The close relationship between male infertility and the consumption of cottonseed products was first found in cotton-producing areas by Shandong scientists in 1971. Further study found that gossypol impaired the sperm quality significantly in rat, rabbit, and so on. Mechanism study showed that gossypol could interact with sperm and then trigger a cascade reaction for different stages of spermatogenesis. Acetate gossypol showed similar biological activities with gossypol. The clinical trial for gossypol tablet for the male contraceptive treatment was initiated in the 1973, which was produced in Shanghai, and the raw material was provided from Shanghai, Shandong, and Zhejiang province. During 1981–1985, the side effect, antifertility reversibility, and safety evaluation induced by gossypol were further investigated by the national 65-35-2-5 scientific group, which was carried out by prospective clinical study in 390 volunteers, and the results showed that there is no carcinogenic, teratogenic, and mutagenic effects in gossypol .

Uses

Different sources of media describe the Uses of 303-45-7 differently. You can refer to the following data:
1. antispermatogenic, antineoplastic, antiHIV
2. Gossypol acts as an inhibitor for several dehydrogenase enzymes. Gossypol has also long been known to possess antimalarial properties. Gossypol provided reliable contraception. gossypol provokes infertility and causes spermatogenesis. Gossypol is used as an active antifertility agent in a variety of male animals, including mice, rats, hamsters, monkeys, rabbits, and bulls.

Indications

This product as gossypol acetate is recorded in the tenth volume of national standards for chemical drugs. Solid formulations include compound acetate gossypol tablets and gossypol potassium chloride vitamin B capsule. Gossypol was used as male contraceptive drug in clinic previously but terminated due to the induced severer hypokalemia. Now, compound acetate gossypol tablets consisted of acetate gossypol and potassium chloride, vitamins are used for the treatment of uterine functional bleeding, uterine fibroids, and menorrhagia and endometriosis.

General Description

Gossypol is considered as an antifertility agent. It is present in cottonseed as a yellowish pigment. This reactive sesquiterpene aldehyde is present in the family Malvaceae and has a molecular mass of 518.54.

Hazard

Toxic by ingestion but is inactivated by heat, 0.04% max allowed in foods.

Biological Activity

Lipophilic agent derived from cottonseed. Exhibits multiple biological effects including antifertility and anticancer activity. Pro-apoptotic; downregulates Bcl-2 and Bcl-XL.

Biochem/physiol Actions

Gossypol is a male antifertility agent and PAF antagonist/inhibitor. Gossypol is a poisonous pigment found in cottonseed and its name is derived from the botanical name of the cotton plant, Gossypium.. Gossypium is extracted from selected hybrid species between two Gossypium species, Gossypium hirsutum and Gossypium barbadens. As a PAF antagonist/inhibitor, Gossypium markedly inhibited the contractile responses of guinea pig lung parenchyma strips stimulated with leukotriene B4, seukotriene D4, and PAF-acether.

Pharmacology

There are significant differences in pharmacological effects of gossypol between male and female. In males, gossypol could significantly reduce sperm quality, as manifested by the reduced sperm density or activity. Mechanism study showed that gossypol could impair spermatogenic epithelium directly, and sperm cells and spermatocytes are the most sensitive. In female, gossypol could inhibit ovarian and endometrial, muscular steroid hormone receptor, hence thinning the endometrium and muscle layer and reducing menstrual flow ; therefore, gossypol acetate and potassium chloride, vitamins, and other combinations were prepared for the compound acetate gossypol tablets, which were used for the treatment of uterine functional bleeding, uterine fibroids, menorrhagia, and uterus endometriosis. The recommended daily oral dose is 20 mg. Gossypol dextrorate has no effect, with levorotate as the active ingredient; therefore, the role of L-gossypol is two times that of gossypol .A good antitumor effect of gossypol and its derivatives was found in recent studies. Gossypol showed significant inhibition on cancer cell proliferation in vitro studies, including tumor cells derived from lymphatic and granulocytes, adrenal glands, breast, and cervical, rectal, and central nervous system. Studies have suggested that gossypol inhibits the catalytic activity of topoisomerase II and intervenes in the stability of topoisomerase – DNA complexes. Gossypol blocks the cell in S stage by reducing the activity of DNA polymerase alpha and beta and inhibiting DNA synthesis. Gossypol is a specific DNA synthesis inhibitor that inhibits cell division. In addition, gossypol can also exhibit antitumor effect by acting as a signal pathway regulator and inhibiting the energy metabolism of tumor cells .

Clinical Use

Due to the presence of hypokalemia and irreversible antifertility risk of gossypol, the clinical indications of male contraceptives are not approved by the Chinese Food and Drug Administration. At present, gossypol and its derivatives are mainly used for female uterine fibroids, functional uterine bleeding, and endometriosis treatment. In addition, the treatment of gossypol and its derivatives in the tumor is gradually confirmed clinically, such as gossypol combined with docetaxel or cisplatin for the treatment of malignant non-small cell lung cancer, and is currently in phase III clinical trial . Gossypol combined with rituximab can achieve better therapeutic efficacy against granulocytic leukemia and is currently in phase II clinical trials .

in vitro

in bovine granulosa cells, treatment with gossypol dose-dependently decreased hcg-induced camp formation. gossypol (12.5 μg/ml) inhibited basal camp level and progesterone secretion(2). gossypol (50 and 100 μg/ml) decreased the percentage of sperm that completed the swim-up procedure. when cultured with5 or 10 μg/ml gossypol, development of cleaved embryos was reduced(3). in the lymphocytes isolated from lymph nodes of balb/c mice, gossypol significantly inhibited the proliferation of mouse lymphocytes stimulated with phorbol ester plus ionomycin in a dose-dependent manner. gossypol significantly suppressed the lymphoblastic transformation of both t and b lymphocyte subsets. moreover, gossypol could induce apoptosis of lymphocytes in a time- and dose-dependent manner (4).

in vivo

in male sprague-dawley rats, gossypol (25 mg/kg, i.p.) caused marked changes in the activity of the hepatic and serum γ-glutamyltransferase (ggt) and microsomal monooxygenases (5). rats that received lower gossypol doses (15 mg/kg/day for four weeks or 30 mg/kg/day for two weeks) showed morphological changes in the liver(6).

references

[1]. gadelha i c n, fonseca n b s, oloris s c s, et al. gossypol toxicity from cottonseed products[j]. the scientific world journal, 2014, 2014.[2]. lin y c, coskun s, sanbuissho a. effects of gossypol on in vitro bovine oocyte maturation and steroidogenesis in bovine granulosa cells[j]. theriogenology, 1994, 41(8): 1601-1611.[3]. brocas c, rivera r m, paula-lopes f f, et al. deleterious actions of gossypol on bovine spermatozoa, oocytes, and embryos[j]. biology of reproduction, 1997, 57(4): 901-907.[4]. xu w, xu l, lu h, et al. the immunosuppressive effect of gossypol in mice is mediated by inhibition of lymphocyte proliferation and by induction of cell apoptosis[j]. actapharmacologicasinica, 2009, 30(5): 597-604.[5]. deoras d p, young-curtis p, dalvi r r, et al. effect of gossypol on hepatic and serum γ-glutamyltransferase activity in rats[j]. veterinary research communications, 1997, 21(5): 317-323.[6]. ying w, hai-peng l. hepatotoxicity of gossypol in rats[j]. journal of ethnopharmacology, 1987, 20(1): 53-64.

Check Digit Verification of cas no

The CAS Registry Mumber 303-45-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,0 and 3 respectively; the second part has 2 digits, 4 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 303-45:
(5*3)+(4*0)+(3*3)+(2*4)+(1*5)=37
37 % 10 = 7
So 303-45-7 is a valid CAS Registry Number.
InChI:InChI=1/C30H30O8/c1-11(2)19-15-7-13(5)21(27(35)23(15)17(9-31)25(33)29(19)37)22-14(6)8-16-20(12(3)4)30(38)26(34)18(10-32)24(16)28(22)36/h7-12,33-38H,1-6H3

303-45-7 Well-known Company Product Price

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  • Sigma

  • (G8761)  (±)-Gossypol from cotton seeds  ≥95% (HPLC)

  • 303-45-7

  • G8761-100MG

  • 1,749.15CNY

  • Detail
  • Sigma

  • (G8761)  (±)-Gossypol from cotton seeds  ≥95% (HPLC)

  • 303-45-7

  • G8761-250MG

  • 3,834.09CNY

  • Detail

303-45-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name GOSSYPOL

1.2 Other means of identification

Product number -
Other names 2,2'-BI[8-FORMYL-1,6,7-TRIHYDROXY-5-ISOPROPYL-3-METHYLNAPHTHALENE]

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:303-45-7 SDS

303-45-7Synthetic route

(±)-gossypol acetic acid
5453-04-3, 866541-93-7, 1189561-66-7

(±)-gossypol acetic acid

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
With iron(III) chloride In acetone at 60℃;85%
In diethyl ether; water at 25℃; for 0.166667h; Temperature; Solvent; Sonication;105 mg
2,3,8-trihydroxy-4-isopropyl-6-methyl-1-naphthaldehyde
40817-07-0

2,3,8-trihydroxy-4-isopropyl-6-methyl-1-naphthaldehyde

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
With tert-butyl peroxyacetate In 1,2-dichloro-ethane at 80℃; for 4h; Inert atmosphere;76.1%
With tert-butyl peroxyacetate In 1,2-dichloro-ethane at 80℃; for 2.5h; Temperature; Inert atmosphere;52%
With tert-butyl peroxyacetate In 1,2-dichloro-ethane; mineral oil at 80℃; for 2.5h; Inert atmosphere; Schlenk technique;41%
With laccase of Coriolus versicolor; oxygen at 30℃; pH=5.5; aq. phosphate buffer;
apogossypol
784206-41-3

apogossypol

N,N'-diphenylformamidine
864131-95-3

N,N'-diphenylformamidine

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
With hydroquinone at 180℃; under 5 - 15 Torr; for 2.5h;72%
apogossypol
784206-41-3

apogossypol

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
With Dichloromethyl methyl ether; titanium tetrachloride In dichloromethane at 0 - 20℃; for 5h; Inert atmosphere;37%
4,4'-dihydroxy-5,5'-diisopropyl-7,7'-dimethyl-bis(3H-naphtho[1,8-bc]furan-3-one)
73728-76-4

4,4'-dihydroxy-5,5'-diisopropyl-7,7'-dimethyl-bis(3H-naphtho[1,8-bc]furan-3-one)

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
In water; acetone for 48h;
Conditions
ConditionsYield
With hydrogenchloride In ethanol at 25℃; Kinetics; Mechanism; Thermodynamic data; other temperatures, ΔH(excit.), ΔS(excit.), ΔG(excit.);
sulfuric acid
7664-93-9

sulfuric acid

dianilogossipol
6952-36-9

dianilogossipol

(rac)-gossypol
303-45-7

(rac)-gossypol

3-(1H-indol-3-yl)-2-[(1,6,1',6'-tetrahydroxy-8'-{[2-(1H-indol-3-yl)-1-methoxycarbonyl-ethylamino]-methylene}-5,5'-diisopropyl-3,3'-dimethyl-7,7'-dioxo-7',8'-dihydro-7H-[2,2']binaphthalenyl-8-ylidenemethyl)-amino]-propionic acid methyl ester

3-(1H-indol-3-yl)-2-[(1,6,1',6'-tetrahydroxy-8'-{[2-(1H-indol-3-yl)-1-methoxycarbonyl-ethylamino]-methylene}-5,5'-diisopropyl-3,3'-dimethyl-7,7'-dioxo-7',8'-dihydro-7H-[2,2']binaphthalenyl-8-ylidenemethyl)-amino]-propionic acid methyl ester

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
With hydrogenchloride; acetic acid In diethyl ether Heating;
C54H54N4O10

C54H54N4O10

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
With hydrogenchloride; acetic acid In diethyl ether Heating;
4-isopropyl-3,8-dimethoxy-1,6-dimethylnaphthalen-2-ol

4-isopropyl-3,8-dimethoxy-1,6-dimethylnaphthalen-2-ol

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: silver(l) oxide / methanol / 3 h / 20 °C
2: potassium carbonate / acetone / 5 h / 20 °C
3: dichloromethane / 0.5 h / 20 °C
4: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
5: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
6: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
7: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 7 steps
1: silver(l) oxide / 2 h / Reflux
2: potassium carbonate / acetone / 5 h / 20 °C
3: dichloromethane / 0.5 h / 20 °C
4: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
5: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
6: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
7: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 8 steps
1: silver(l) oxide / methanol / 3 h / 20 °C
2: potassium carbonate / acetone / 5 h / 20 °C
3: dichloromethane / 0.5 h / 20 °C
4: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
5: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
6: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
7: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
8: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 8 steps
1: silver(l) oxide / 2 h / Reflux
2: potassium carbonate / acetone / 5 h / 20 °C
3: dichloromethane / 0.5 h / 20 °C
4: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
5: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
6: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
7: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
8: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
C18H24O4

C18H24O4

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: potassium carbonate / acetone / 5 h / 20 °C
2: dichloromethane / 0.5 h / 20 °C
3: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
4: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
5: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
6: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 7 steps
1: potassium carbonate / acetone / 5 h / 20 °C
2: dichloromethane / 0.5 h / 20 °C
3: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
4: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
5: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
6: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
7: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
1-isopropyl-2,3,5-trimethoxy-4-(methoxymethyl)-7-methylnaphthalene

1-isopropyl-2,3,5-trimethoxy-4-(methoxymethyl)-7-methylnaphthalene

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: dichloromethane / 0.5 h / 20 °C
2: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
4: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
5: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 6 steps
1: dichloromethane / 0.5 h / 20 °C
2: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
4: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
5: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
6: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere; Schlenk technique
1.2: 20 °C / Inert atmosphere; Schlenk technique
2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C / Inert atmosphere; Schlenk technique
3.1: boron tribromide / dichloromethane / 10 h / -78 - -10 °C / Inert atmosphere; Schlenk technique
4.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane; mineral oil / 2.5 h / 80 °C / Inert atmosphere; Schlenk technique
View Scheme
Multi-step reaction with 4 steps
1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
2: 2-Iodobenzoic acid / dimethyl sulfoxide / 12 h
3: boron tribromide / dichloromethane / 10 h / -78 - -10 °C
4: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 2.5 h / 80 °C / Inert atmosphere
View Scheme
(4-isopropyl-2,3,8-trimethoxy-6-methylnaphthalen-1-yl)methanol

(4-isopropyl-2,3,8-trimethoxy-6-methylnaphthalen-1-yl)methanol

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
2: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
3: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
2: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
3: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
4: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C / Inert atmosphere; Schlenk technique
2: boron tribromide / dichloromethane / 10 h / -78 - -10 °C / Inert atmosphere; Schlenk technique
3: tert-butyl peroxyacetate / 1,2-dichloro-ethane; mineral oil / 2.5 h / 80 °C / Inert atmosphere; Schlenk technique
View Scheme
Multi-step reaction with 3 steps
1: 2-Iodobenzoic acid / dimethyl sulfoxide / 12 h
2: boron tribromide / dichloromethane / 10 h / -78 - -10 °C
3: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 2.5 h / 80 °C / Inert atmosphere
View Scheme
4-isopropyl-2,3,8-trimethoxy-6-methyl-1-naphthaldehyde
50399-96-7

4-isopropyl-2,3,8-trimethoxy-6-methyl-1-naphthaldehyde

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
2: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
2: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
3: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: boron tribromide / dichloromethane / 10 h / -78 - -10 °C / Inert atmosphere; Schlenk technique
2: tert-butyl peroxyacetate / 1,2-dichloro-ethane; mineral oil / 2.5 h / 80 °C / Inert atmosphere; Schlenk technique
View Scheme
Multi-step reaction with 2 steps
1: boron tribromide / dichloromethane / 10 h / -78 - -10 °C
2: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 2.5 h / 80 °C / Inert atmosphere
View Scheme
4-hydroxy-5-isopropyl-7-methylnaphtho[1,8-bc]furan-3-one
1256723-09-7

4-hydroxy-5-isopropyl-7-methylnaphtho[1,8-bc]furan-3-one

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
2: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
2-hydroxy-6-isopropyl-3-methyl-benzaldehyde
1665-99-2

2-hydroxy-6-isopropyl-3-methyl-benzaldehyde

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 17 steps
1.1: acetic acid; bromine / 20.25 h / 20 °C / Cooling with ice
2.1: potassium carbonate / acetone / 15 h / 30 °C
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
3.2: 2 h / Reflux
4.1: potassium carbonate / acetone / 12 h / 20 °C
5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
5.2: 10 h / -78 - -30 °C / Inert atmosphere
6.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
7.1: acetic anhydride; sodium acetate / 2 h / Reflux
8.1: sodium hydroxide / methanol; water / Reflux
9.1: potassium carbonate / acetone / 12 h / 20 °C
10.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
10.2: 10 h / 20 °C
11.1: silver(l) oxide / methanol / 3 h / 20 °C
12.1: potassium carbonate / acetone / 5 h / 20 °C
13.1: dichloromethane / 0.5 h / 20 °C
14.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
15.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
16.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
17.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 17 steps
1.1: acetic acid; bromine / 20.25 h / 20 °C / Cooling with ice
2.1: potassium carbonate / acetone / 15 h / 30 °C
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
3.2: 2 h / Reflux
4.1: potassium carbonate / acetone / 12 h / 20 °C
5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
5.2: 10 h / -78 - -30 °C / Inert atmosphere
6.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
7.1: acetic anhydride; sodium acetate / 2 h / Reflux
8.1: sodium hydroxide / methanol; water / Reflux
9.1: potassium carbonate / acetone / 12 h / 20 °C
10.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
10.2: 10 h / 20 °C
11.1: silver(l) oxide / 2 h / Reflux
12.1: potassium carbonate / acetone / 5 h / 20 °C
13.1: dichloromethane / 0.5 h / 20 °C
14.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
15.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
16.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
17.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 18 steps
1.1: acetic acid; bromine / 20.25 h / 20 °C / Cooling with ice
2.1: potassium carbonate / acetone / 15 h / 30 °C
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
3.2: 2 h / Reflux
4.1: potassium carbonate / acetone / 12 h / 20 °C
5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
5.2: 10 h / -78 - -30 °C / Inert atmosphere
6.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
7.1: acetic anhydride; sodium acetate / 2 h / Reflux
8.1: sodium hydroxide / methanol; water / Reflux
9.1: potassium carbonate / acetone / 12 h / 20 °C
10.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
10.2: 10 h / 20 °C
11.1: silver(l) oxide / methanol / 3 h / 20 °C
12.1: potassium carbonate / acetone / 5 h / 20 °C
13.1: dichloromethane / 0.5 h / 20 °C
14.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
15.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
16.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
17.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
18.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 18 steps
1.1: acetic acid; bromine / 20.25 h / 20 °C / Cooling with ice
2.1: potassium carbonate / acetone / 15 h / 30 °C
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
3.2: 2 h / Reflux
4.1: potassium carbonate / acetone / 12 h / 20 °C
5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
5.2: 10 h / -78 - -30 °C / Inert atmosphere
6.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
7.1: acetic anhydride; sodium acetate / 2 h / Reflux
8.1: sodium hydroxide / methanol; water / Reflux
9.1: potassium carbonate / acetone / 12 h / 20 °C
10.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
10.2: 10 h / 20 °C
11.1: silver(l) oxide / 2 h / Reflux
12.1: potassium carbonate / acetone / 5 h / 20 °C
13.1: dichloromethane / 0.5 h / 20 °C
14.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
15.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
16.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
17.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
18.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
carvacrol
499-75-2

carvacrol

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 18 steps
1.1: tin(IV) chloride; triethylamine / toluene / 0.33 h / 20 °C / Inert atmosphere
1.2: 8 h / 100 °C / Inert atmosphere
2.1: acetic acid; bromine / 20.25 h / 20 °C / Cooling with ice
3.1: potassium carbonate / acetone / 15 h / 30 °C
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
4.2: 2 h / Reflux
5.1: potassium carbonate / acetone / 12 h / 20 °C
6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
6.2: 10 h / -78 - -30 °C / Inert atmosphere
7.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
8.1: acetic anhydride; sodium acetate / 2 h / Reflux
9.1: sodium hydroxide / methanol; water / Reflux
10.1: potassium carbonate / acetone / 12 h / 20 °C
11.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
11.2: 10 h / 20 °C
12.1: silver(l) oxide / methanol / 3 h / 20 °C
13.1: potassium carbonate / acetone / 5 h / 20 °C
14.1: dichloromethane / 0.5 h / 20 °C
15.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
16.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
17.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
18.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 18 steps
1.1: tin(IV) chloride; triethylamine / toluene / 0.33 h / 20 °C / Inert atmosphere
1.2: 8 h / 100 °C / Inert atmosphere
2.1: acetic acid; bromine / 20.25 h / 20 °C / Cooling with ice
3.1: potassium carbonate / acetone / 15 h / 30 °C
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
4.2: 2 h / Reflux
5.1: potassium carbonate / acetone / 12 h / 20 °C
6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
6.2: 10 h / -78 - -30 °C / Inert atmosphere
7.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
8.1: acetic anhydride; sodium acetate / 2 h / Reflux
9.1: sodium hydroxide / methanol; water / Reflux
10.1: potassium carbonate / acetone / 12 h / 20 °C
11.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
11.2: 10 h / 20 °C
12.1: silver(l) oxide / 2 h / Reflux
13.1: potassium carbonate / acetone / 5 h / 20 °C
14.1: dichloromethane / 0.5 h / 20 °C
15.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
16.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
17.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
18.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 19 steps
1.1: tin(IV) chloride; triethylamine / toluene / 0.33 h / 20 °C / Inert atmosphere
1.2: 8 h / 100 °C / Inert atmosphere
2.1: acetic acid; bromine / 20.25 h / 20 °C / Cooling with ice
3.1: potassium carbonate / acetone / 15 h / 30 °C
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
4.2: 2 h / Reflux
5.1: potassium carbonate / acetone / 12 h / 20 °C
6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
6.2: 10 h / -78 - -30 °C / Inert atmosphere
7.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
8.1: acetic anhydride; sodium acetate / 2 h / Reflux
9.1: sodium hydroxide / methanol; water / Reflux
10.1: potassium carbonate / acetone / 12 h / 20 °C
11.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
11.2: 10 h / 20 °C
12.1: silver(l) oxide / methanol / 3 h / 20 °C
13.1: potassium carbonate / acetone / 5 h / 20 °C
14.1: dichloromethane / 0.5 h / 20 °C
15.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
16.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
17.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
18.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
19.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 19 steps
1.1: tin(IV) chloride; triethylamine / toluene / 0.33 h / 20 °C / Inert atmosphere
1.2: 8 h / 100 °C / Inert atmosphere
2.1: acetic acid; bromine / 20.25 h / 20 °C / Cooling with ice
3.1: potassium carbonate / acetone / 15 h / 30 °C
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
4.2: 2 h / Reflux
5.1: potassium carbonate / acetone / 12 h / 20 °C
6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
6.2: 10 h / -78 - -30 °C / Inert atmosphere
7.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
8.1: acetic anhydride; sodium acetate / 2 h / Reflux
9.1: sodium hydroxide / methanol; water / Reflux
10.1: potassium carbonate / acetone / 12 h / 20 °C
11.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
11.2: 10 h / 20 °C
12.1: silver(l) oxide / 2 h / Reflux
13.1: potassium carbonate / acetone / 5 h / 20 °C
14.1: dichloromethane / 0.5 h / 20 °C
15.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
16.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
17.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
18.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
19.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
C11H13BrO2

C11H13BrO2

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 16 steps
1.1: potassium carbonate / acetone / 15 h / 30 °C
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
2.2: 2 h / Reflux
3.1: potassium carbonate / acetone / 12 h / 20 °C
4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
4.2: 10 h / -78 - -30 °C / Inert atmosphere
5.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
6.1: acetic anhydride; sodium acetate / 2 h / Reflux
7.1: sodium hydroxide / methanol; water / Reflux
8.1: potassium carbonate / acetone / 12 h / 20 °C
9.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
9.2: 10 h / 20 °C
10.1: silver(l) oxide / methanol / 3 h / 20 °C
11.1: potassium carbonate / acetone / 5 h / 20 °C
12.1: dichloromethane / 0.5 h / 20 °C
13.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
14.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
15.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
16.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 16 steps
1.1: potassium carbonate / acetone / 15 h / 30 °C
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
2.2: 2 h / Reflux
3.1: potassium carbonate / acetone / 12 h / 20 °C
4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
4.2: 10 h / -78 - -30 °C / Inert atmosphere
5.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
6.1: acetic anhydride; sodium acetate / 2 h / Reflux
7.1: sodium hydroxide / methanol; water / Reflux
8.1: potassium carbonate / acetone / 12 h / 20 °C
9.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
9.2: 10 h / 20 °C
10.1: silver(l) oxide / 2 h / Reflux
11.1: potassium carbonate / acetone / 5 h / 20 °C
12.1: dichloromethane / 0.5 h / 20 °C
13.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
14.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
15.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
16.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 17 steps
1.1: potassium carbonate / acetone / 15 h / 30 °C
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
2.2: 2 h / Reflux
3.1: potassium carbonate / acetone / 12 h / 20 °C
4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
4.2: 10 h / -78 - -30 °C / Inert atmosphere
5.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
6.1: acetic anhydride; sodium acetate / 2 h / Reflux
7.1: sodium hydroxide / methanol; water / Reflux
8.1: potassium carbonate / acetone / 12 h / 20 °C
9.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
9.2: 10 h / 20 °C
10.1: silver(l) oxide / methanol / 3 h / 20 °C
11.1: potassium carbonate / acetone / 5 h / 20 °C
12.1: dichloromethane / 0.5 h / 20 °C
13.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
14.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
15.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
16.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
17.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 17 steps
1.1: potassium carbonate / acetone / 15 h / 30 °C
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
2.2: 2 h / Reflux
3.1: potassium carbonate / acetone / 12 h / 20 °C
4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
4.2: 10 h / -78 - -30 °C / Inert atmosphere
5.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
6.1: acetic anhydride; sodium acetate / 2 h / Reflux
7.1: sodium hydroxide / methanol; water / Reflux
8.1: potassium carbonate / acetone / 12 h / 20 °C
9.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
9.2: 10 h / 20 °C
10.1: silver(l) oxide / 2 h / Reflux
11.1: potassium carbonate / acetone / 5 h / 20 °C
12.1: dichloromethane / 0.5 h / 20 °C
13.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
14.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
15.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
16.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
17.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
C24H26O5

C24H26O5

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: potassium carbonate / acetone / 12 h / 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
2.2: 10 h / 20 °C
3.1: silver(l) oxide / methanol / 3 h / 20 °C
4.1: potassium carbonate / acetone / 5 h / 20 °C
5.1: dichloromethane / 0.5 h / 20 °C
6.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
8.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
9.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
10.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 10 steps
1.1: potassium carbonate / acetone / 12 h / 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
2.2: 10 h / 20 °C
3.1: silver(l) oxide / 2 h / Reflux
4.1: potassium carbonate / acetone / 5 h / 20 °C
5.1: dichloromethane / 0.5 h / 20 °C
6.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
8.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
9.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
10.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 9 steps
1.1: potassium carbonate / acetone / 12 h / 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
2.2: 10 h / 20 °C
3.1: silver(l) oxide / 2 h / Reflux
4.1: potassium carbonate / acetone / 5 h / 20 °C
5.1: dichloromethane / 0.5 h / 20 °C
6.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
8.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
9.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 9 steps
1.1: potassium carbonate / acetone / 12 h / 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
2.2: 10 h / 20 °C
3.1: silver(l) oxide / methanol / 3 h / 20 °C
4.1: potassium carbonate / acetone / 5 h / 20 °C
5.1: dichloromethane / 0.5 h / 20 °C
6.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
8.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
9.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
C18H19BrO2

C18H19BrO2

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 15 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
1.2: 2 h / Reflux
2.1: potassium carbonate / acetone / 12 h / 20 °C
3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
3.2: 10 h / -78 - -30 °C / Inert atmosphere
4.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
5.1: acetic anhydride; sodium acetate / 2 h / Reflux
6.1: sodium hydroxide / methanol; water / Reflux
7.1: potassium carbonate / acetone / 12 h / 20 °C
8.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
8.2: 10 h / 20 °C
9.1: silver(l) oxide / methanol / 3 h / 20 °C
10.1: potassium carbonate / acetone / 5 h / 20 °C
11.1: dichloromethane / 0.5 h / 20 °C
12.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
13.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
14.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
15.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 15 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
1.2: 2 h / Reflux
2.1: potassium carbonate / acetone / 12 h / 20 °C
3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
3.2: 10 h / -78 - -30 °C / Inert atmosphere
4.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
5.1: acetic anhydride; sodium acetate / 2 h / Reflux
6.1: sodium hydroxide / methanol; water / Reflux
7.1: potassium carbonate / acetone / 12 h / 20 °C
8.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
8.2: 10 h / 20 °C
9.1: silver(l) oxide / 2 h / Reflux
10.1: potassium carbonate / acetone / 5 h / 20 °C
11.1: dichloromethane / 0.5 h / 20 °C
12.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
13.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
14.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
15.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 16 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
1.2: 2 h / Reflux
2.1: potassium carbonate / acetone / 12 h / 20 °C
3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
3.2: 10 h / -78 - -30 °C / Inert atmosphere
4.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
5.1: acetic anhydride; sodium acetate / 2 h / Reflux
6.1: sodium hydroxide / methanol; water / Reflux
7.1: potassium carbonate / acetone / 12 h / 20 °C
8.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
8.2: 10 h / 20 °C
9.1: silver(l) oxide / methanol / 3 h / 20 °C
10.1: potassium carbonate / acetone / 5 h / 20 °C
11.1: dichloromethane / 0.5 h / 20 °C
12.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
13.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
14.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
15.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
16.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 16 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
1.2: 2 h / Reflux
2.1: potassium carbonate / acetone / 12 h / 20 °C
3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
3.2: 10 h / -78 - -30 °C / Inert atmosphere
4.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
5.1: acetic anhydride; sodium acetate / 2 h / Reflux
6.1: sodium hydroxide / methanol; water / Reflux
7.1: potassium carbonate / acetone / 12 h / 20 °C
8.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
8.2: 10 h / 20 °C
9.1: silver(l) oxide / 2 h / Reflux
10.1: potassium carbonate / acetone / 5 h / 20 °C
11.1: dichloromethane / 0.5 h / 20 °C
12.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
13.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
14.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
15.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
16.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
C20H23F3O5

C20H23F3O5

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
3: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
4: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
3: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
4: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
5: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
C17H19BrO2

C17H19BrO2

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1.1: potassium carbonate / acetone / 12 h / 20 °C
2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
2.2: 10 h / -78 - -30 °C / Inert atmosphere
3.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
4.1: acetic anhydride; sodium acetate / 2 h / Reflux
5.1: sodium hydroxide / methanol; water / Reflux
6.1: potassium carbonate / acetone / 12 h / 20 °C
7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
7.2: 10 h / 20 °C
8.1: silver(l) oxide / methanol / 3 h / 20 °C
9.1: potassium carbonate / acetone / 5 h / 20 °C
10.1: dichloromethane / 0.5 h / 20 °C
11.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
12.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
13.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
14.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 14 steps
1.1: potassium carbonate / acetone / 12 h / 20 °C
2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
2.2: 10 h / -78 - -30 °C / Inert atmosphere
3.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
4.1: acetic anhydride; sodium acetate / 2 h / Reflux
5.1: sodium hydroxide / methanol; water / Reflux
6.1: potassium carbonate / acetone / 12 h / 20 °C
7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
7.2: 10 h / 20 °C
8.1: silver(l) oxide / 2 h / Reflux
9.1: potassium carbonate / acetone / 5 h / 20 °C
10.1: dichloromethane / 0.5 h / 20 °C
11.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
12.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
13.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
14.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 15 steps
1.1: potassium carbonate / acetone / 12 h / 20 °C
2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
2.2: 10 h / -78 - -30 °C / Inert atmosphere
3.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
4.1: acetic anhydride; sodium acetate / 2 h / Reflux
5.1: sodium hydroxide / methanol; water / Reflux
6.1: potassium carbonate / acetone / 12 h / 20 °C
7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
7.2: 10 h / 20 °C
8.1: silver(l) oxide / methanol / 3 h / 20 °C
9.1: potassium carbonate / acetone / 5 h / 20 °C
10.1: dichloromethane / 0.5 h / 20 °C
11.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
12.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
13.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
14.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
15.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 15 steps
1.1: potassium carbonate / acetone / 12 h / 20 °C
2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
2.2: 10 h / -78 - -30 °C / Inert atmosphere
3.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
4.1: acetic anhydride; sodium acetate / 2 h / Reflux
5.1: sodium hydroxide / methanol; water / Reflux
6.1: potassium carbonate / acetone / 12 h / 20 °C
7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
7.2: 10 h / 20 °C
8.1: silver(l) oxide / 2 h / Reflux
9.1: potassium carbonate / acetone / 5 h / 20 °C
10.1: dichloromethane / 0.5 h / 20 °C
11.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
12.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
13.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
14.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
15.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
2-(benzyloxy)-5-bromo-4-isopropyl-3-methoxy-1-methylbenzene

2-(benzyloxy)-5-bromo-4-isopropyl-3-methoxy-1-methylbenzene

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
1.2: 10 h / -78 - -30 °C / Inert atmosphere
2.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
3.1: acetic anhydride; sodium acetate / 2 h / Reflux
4.1: sodium hydroxide / methanol; water / Reflux
5.1: potassium carbonate / acetone / 12 h / 20 °C
6.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
6.2: 10 h / 20 °C
7.1: silver(l) oxide / methanol / 3 h / 20 °C
8.1: potassium carbonate / acetone / 5 h / 20 °C
9.1: dichloromethane / 0.5 h / 20 °C
10.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
11.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
12.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
13.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 13 steps
1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
1.2: 10 h / -78 - -30 °C / Inert atmosphere
2.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
3.1: acetic anhydride; sodium acetate / 2 h / Reflux
4.1: sodium hydroxide / methanol; water / Reflux
5.1: potassium carbonate / acetone / 12 h / 20 °C
6.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
6.2: 10 h / 20 °C
7.1: silver(l) oxide / 2 h / Reflux
8.1: potassium carbonate / acetone / 5 h / 20 °C
9.1: dichloromethane / 0.5 h / 20 °C
10.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
11.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
12.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
13.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 14 steps
1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
1.2: 10 h / -78 - -30 °C / Inert atmosphere
2.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
3.1: acetic anhydride; sodium acetate / 2 h / Reflux
4.1: sodium hydroxide / methanol; water / Reflux
5.1: potassium carbonate / acetone / 12 h / 20 °C
6.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
6.2: 10 h / 20 °C
7.1: silver(l) oxide / methanol / 3 h / 20 °C
8.1: potassium carbonate / acetone / 5 h / 20 °C
9.1: dichloromethane / 0.5 h / 20 °C
10.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
11.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
12.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
13.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
14.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 14 steps
1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
1.2: 10 h / -78 - -30 °C / Inert atmosphere
2.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
3.1: acetic anhydride; sodium acetate / 2 h / Reflux
4.1: sodium hydroxide / methanol; water / Reflux
5.1: potassium carbonate / acetone / 12 h / 20 °C
6.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
6.2: 10 h / 20 °C
7.1: silver(l) oxide / 2 h / Reflux
8.1: potassium carbonate / acetone / 5 h / 20 °C
9.1: dichloromethane / 0.5 h / 20 °C
10.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
11.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
12.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
13.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
14.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
C19H22O3

C19H22O3

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
2.1: acetic anhydride; sodium acetate / 2 h / Reflux
3.1: sodium hydroxide / methanol; water / Reflux
4.1: potassium carbonate / acetone / 12 h / 20 °C
5.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
5.2: 10 h / 20 °C
6.1: silver(l) oxide / methanol / 3 h / 20 °C
7.1: potassium carbonate / acetone / 5 h / 20 °C
8.1: dichloromethane / 0.5 h / 20 °C
9.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
10.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
11.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
12.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 12 steps
1.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
2.1: acetic anhydride; sodium acetate / 2 h / Reflux
3.1: sodium hydroxide / methanol; water / Reflux
4.1: potassium carbonate / acetone / 12 h / 20 °C
5.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
5.2: 10 h / 20 °C
6.1: silver(l) oxide / 2 h / Reflux
7.1: potassium carbonate / acetone / 5 h / 20 °C
8.1: dichloromethane / 0.5 h / 20 °C
9.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
10.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
11.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
12.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 13 steps
1.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
2.1: acetic anhydride; sodium acetate / 2 h / Reflux
3.1: sodium hydroxide / methanol; water / Reflux
4.1: potassium carbonate / acetone / 12 h / 20 °C
5.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
5.2: 10 h / 20 °C
6.1: silver(l) oxide / methanol / 3 h / 20 °C
7.1: potassium carbonate / acetone / 5 h / 20 °C
8.1: dichloromethane / 0.5 h / 20 °C
9.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
10.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
11.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
12.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
13.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 13 steps
1.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
2.1: acetic anhydride; sodium acetate / 2 h / Reflux
3.1: sodium hydroxide / methanol; water / Reflux
4.1: potassium carbonate / acetone / 12 h / 20 °C
5.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
5.2: 10 h / 20 °C
6.1: silver(l) oxide / 2 h / Reflux
7.1: potassium carbonate / acetone / 5 h / 20 °C
8.1: dichloromethane / 0.5 h / 20 °C
9.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
10.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
11.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
12.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
13.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
C24H28O6

C24H28O6

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: acetic anhydride; sodium acetate / 2 h / Reflux
2.1: sodium hydroxide / methanol; water / Reflux
3.1: potassium carbonate / acetone / 12 h / 20 °C
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
4.2: 10 h / 20 °C
5.1: silver(l) oxide / methanol / 3 h / 20 °C
6.1: potassium carbonate / acetone / 5 h / 20 °C
7.1: dichloromethane / 0.5 h / 20 °C
8.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
9.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
10.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
11.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 11 steps
1.1: acetic anhydride; sodium acetate / 2 h / Reflux
2.1: sodium hydroxide / methanol; water / Reflux
3.1: potassium carbonate / acetone / 12 h / 20 °C
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
4.2: 10 h / 20 °C
5.1: silver(l) oxide / 2 h / Reflux
6.1: potassium carbonate / acetone / 5 h / 20 °C
7.1: dichloromethane / 0.5 h / 20 °C
8.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
9.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
10.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
11.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 12 steps
1.1: acetic anhydride; sodium acetate / 2 h / Reflux
2.1: sodium hydroxide / methanol; water / Reflux
3.1: potassium carbonate / acetone / 12 h / 20 °C
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
4.2: 10 h / 20 °C
5.1: silver(l) oxide / methanol / 3 h / 20 °C
6.1: potassium carbonate / acetone / 5 h / 20 °C
7.1: dichloromethane / 0.5 h / 20 °C
8.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
9.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
10.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
11.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
12.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 12 steps
1.1: acetic anhydride; sodium acetate / 2 h / Reflux
2.1: sodium hydroxide / methanol; water / Reflux
3.1: potassium carbonate / acetone / 12 h / 20 °C
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
4.2: 10 h / 20 °C
5.1: silver(l) oxide / 2 h / Reflux
6.1: potassium carbonate / acetone / 5 h / 20 °C
7.1: dichloromethane / 0.5 h / 20 °C
8.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
9.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
10.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
11.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
12.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
C26H28O6

C26H28O6

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: sodium hydroxide / methanol; water / Reflux
2.1: potassium carbonate / acetone / 12 h / 20 °C
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
3.2: 10 h / 20 °C
4.1: silver(l) oxide / methanol / 3 h / 20 °C
5.1: potassium carbonate / acetone / 5 h / 20 °C
6.1: dichloromethane / 0.5 h / 20 °C
7.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
9.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
10.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 10 steps
1.1: sodium hydroxide / methanol; water / Reflux
2.1: potassium carbonate / acetone / 12 h / 20 °C
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
3.2: 10 h / 20 °C
4.1: silver(l) oxide / 2 h / Reflux
5.1: potassium carbonate / acetone / 5 h / 20 °C
6.1: dichloromethane / 0.5 h / 20 °C
7.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
9.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
10.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 11 steps
1.1: sodium hydroxide / methanol; water / Reflux
2.1: potassium carbonate / acetone / 12 h / 20 °C
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
3.2: 10 h / 20 °C
4.1: silver(l) oxide / methanol / 3 h / 20 °C
5.1: potassium carbonate / acetone / 5 h / 20 °C
6.1: dichloromethane / 0.5 h / 20 °C
7.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
9.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
10.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
11.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 11 steps
1.1: sodium hydroxide / methanol; water / Reflux
2.1: potassium carbonate / acetone / 12 h / 20 °C
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
3.2: 10 h / 20 °C
4.1: silver(l) oxide / 2 h / Reflux
5.1: potassium carbonate / acetone / 5 h / 20 °C
6.1: dichloromethane / 0.5 h / 20 °C
7.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
9.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
10.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
11.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
methyl 6-(benzyloxy)-8-isopropyl-4,7-dimethoxy-5-methyl-2-naphthoate

methyl 6-(benzyloxy)-8-isopropyl-4,7-dimethoxy-5-methyl-2-naphthoate

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
1.2: 10 h / 20 °C
2.1: silver(l) oxide / 2 h / Reflux
3.1: potassium carbonate / acetone / 5 h / 20 °C
4.1: dichloromethane / 0.5 h / 20 °C
5.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
7.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
8.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 8 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
1.2: 10 h / 20 °C
2.1: silver(l) oxide / methanol / 3 h / 20 °C
3.1: potassium carbonate / acetone / 5 h / 20 °C
4.1: dichloromethane / 0.5 h / 20 °C
5.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
7.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
8.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 9 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
1.2: 10 h / 20 °C
2.1: silver(l) oxide / 2 h / Reflux
3.1: potassium carbonate / acetone / 5 h / 20 °C
4.1: dichloromethane / 0.5 h / 20 °C
5.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
7.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
8.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
9.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 9 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
1.2: 10 h / 20 °C
2.1: silver(l) oxide / methanol / 3 h / 20 °C
3.1: potassium carbonate / acetone / 5 h / 20 °C
4.1: dichloromethane / 0.5 h / 20 °C
5.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
7.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
8.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
9.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
C24H30O5

C24H30O5

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1.1: sodium tetrahydroborate; methanol / 0.5 h / 0 °C / Inert atmosphere; Schlenk technique
2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.75 h / 0 °C / Inert atmosphere; Schlenk technique
2.2: 14 h / 0 - 20 °C / Inert atmosphere; Schlenk technique
3.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 32 h / 20 °C / Schlenk technique
4.1: potassium tert-butylate / tetrahydrofuran / 0.75 h / 0 - 20 °C / Inert atmosphere; Schlenk technique
4.2: 2 h / 20 °C / Inert atmosphere; Schlenk technique
5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 4 h / 20 °C / Inert atmosphere; Schlenk technique
6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C / Inert atmosphere; Schlenk technique
7.1: 2,6-di-tert-butyl-4-methyl-phenol / chlorobenzene / 13 h / 160 °C / Schlenk technique; Inert atmosphere
8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C / Inert atmosphere; Schlenk technique
9.1: potassium carbonate / acetonitrile / 20 h / 80 °C / Inert atmosphere; Schlenk technique
10.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere; Schlenk technique
10.2: 20 °C / Inert atmosphere; Schlenk technique
11.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C / Inert atmosphere; Schlenk technique
12.1: boron tribromide / dichloromethane / 10 h / -78 - -10 °C / Inert atmosphere; Schlenk technique
13.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane; mineral oil / 2.5 h / 80 °C / Inert atmosphere; Schlenk technique
View Scheme
C18H24O4

C18H24O4

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: potassium carbonate / acetonitrile / 20 h / 80 °C / Inert atmosphere; Schlenk technique
2.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere; Schlenk technique
2.2: 20 °C / Inert atmosphere; Schlenk technique
3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C / Inert atmosphere; Schlenk technique
4.1: boron tribromide / dichloromethane / 10 h / -78 - -10 °C / Inert atmosphere; Schlenk technique
5.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane; mineral oil / 2.5 h / 80 °C / Inert atmosphere; Schlenk technique
View Scheme
Multi-step reaction with 5 steps
1: potassium carbonate / acetonitrile / 4 h / 80 °C
2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
3: 2-Iodobenzoic acid / dimethyl sulfoxide / 12 h
4: boron tribromide / dichloromethane / 10 h / -78 - -10 °C
5: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 2.5 h / 80 °C / Inert atmosphere
View Scheme
(rac)-gossypol
303-45-7

(rac)-gossypol

L-Phenylalaninol
3182-95-4

L-Phenylalaninol

8,8'-Bis-((S)-4-benzyl-oxazolidin-2-yl)-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

8,8'-Bis-((S)-4-benzyl-oxazolidin-2-yl)-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

Conditions
ConditionsYield
In methanol for 5h; Ambient temperature;100%
(rac)-gossypol
303-45-7

(rac)-gossypol

C54H54N4O10

C54H54N4O10

C54H54N4O10

C54H54N4O10

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 45℃; for 2h; Resolution of racemate;A 99.4%
B 95%
heptane-1,7-diamine
646-19-5

heptane-1,7-diamine

(rac)-gossypol
303-45-7

(rac)-gossypol

8,8'-Bis-[1-(7-amino-heptylamino)-meth-(Z)-ylidene]-1,6,1',6'-tetrahydroxy-5,5'-diisopropyl-3,3'-dimethyl-8H,8'H-[2,2']binaphthalenyl-7,7'-dione

8,8'-Bis-[1-(7-amino-heptylamino)-meth-(Z)-ylidene]-1,6,1',6'-tetrahydroxy-5,5'-diisopropyl-3,3'-dimethyl-8H,8'H-[2,2']binaphthalenyl-7,7'-dione

Conditions
ConditionsYield
With acid In ethanol for 3h; Heating;98.7%
(rac)-gossypol
303-45-7

(rac)-gossypol

Glycyrrhizin ammonium
53956-04-0

Glycyrrhizin ammonium

C42H62O16*C30H30O8*H3N

C42H62O16*C30H30O8*H3N

Conditions
ConditionsYield
at 20℃;98%
(rac)-gossypol
303-45-7

(rac)-gossypol

C54H54N4O10

C54H54N4O10

Conditions
ConditionsYield
With sodium hydroxide In ethanol Reflux;98%
(rac)-gossypol
303-45-7

(rac)-gossypol

C54H54N4O10
132303-09-4

C54H54N4O10

Conditions
ConditionsYield
With sodium hydroxide In ethanol Reflux;98%
(rac)-gossypol
303-45-7

(rac)-gossypol

C54H54N4O10

C54H54N4O10

C54H54N4O10

C54H54N4O10

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 20℃; for 0.5h;A 97%
B 94%
(rac)-gossypol
303-45-7

(rac)-gossypol

ethylamine
75-04-7

ethylamine

1,6,7,1',6',7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthyl-8,8'-dicarbaldehyde bis-ethylimine
307976-02-9

1,6,7,1',6',7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthyl-8,8'-dicarbaldehyde bis-ethylimine

Conditions
ConditionsYield
In diethyl ether; isopropyl alcohol at 20 - 45℃; for 2.08333h; Condensation;96%
With isopropyl alcohol
(rac)-gossypol
303-45-7

(rac)-gossypol

isopropylamine
75-31-0

isopropylamine

5,5'-Diisopropyl-8,8'-bis-[(E)-isopropylimino-methyl]-3,3'-dimethyl-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

5,5'-Diisopropyl-8,8'-bis-[(E)-isopropylimino-methyl]-3,3'-dimethyl-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

Conditions
ConditionsYield
In diethyl ether; isopropyl alcohol at 20 - 45℃; for 2.08333h; Condensation;96%
(rac)-gossypol
303-45-7

(rac)-gossypol

megosin

megosin

Conditions
ConditionsYield
With sodium hydroxide In ethanol for 3h; Heating;95.8%
(rac)-gossypol
303-45-7

(rac)-gossypol

5-Aminosalicylic Acid
89-57-6

5-Aminosalicylic Acid

gossypolydenebis-N-(3-carboxy-4-hydroxyaniline)

gossypolydenebis-N-(3-carboxy-4-hydroxyaniline)

Conditions
ConditionsYield
In ethanol for 3h; Heating;95.31%
(rac)-gossypol
303-45-7

(rac)-gossypol

apogossypol
784206-41-3

apogossypol

Conditions
ConditionsYield
Stage #1: (rac)-gossypol With sodium hydroxide; acetic acid In water at 90℃; for 3.5h; darkness;
Stage #2: With sulfuric acid In water at 0℃;
95%
Stage #1: (rac)-gossypol With water; sodium hydroxide at 90℃; for 3.5h; Inert atmosphere; Darkness;
Stage #2: With sulfuric acid In water Cooling with ice;
95%
Stage #1: (rac)-gossypol With sodium hydroxide In water at 90℃; for 3.5h; Inert atmosphere; Darkness;
Stage #2: With sulfuric acid In water
95%
(rac)-gossypol
303-45-7

(rac)-gossypol

methylamine
74-89-5

methylamine

5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-[(E)-methyliminomethyl]-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-[(E)-methyliminomethyl]-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

Conditions
ConditionsYield
In N,N-dimethyl-formamide Condensation;95%
(rac)-gossypol
303-45-7

(rac)-gossypol

4-hydroxynon-2-enal
850480-50-1

4-hydroxynon-2-enal

5,5'-dihydroxy-2,2'-bis((E)-3-hydroxyoct-1-en-1-yl)-9,9'-diisopropyl-7,7'-dimethyl-[6,6'-binaphtho[2,3-d][1,3]dioxole]-4,4'-dicarbaldehyde

5,5'-dihydroxy-2,2'-bis((E)-3-hydroxyoct-1-en-1-yl)-9,9'-diisopropyl-7,7'-dimethyl-[6,6'-binaphtho[2,3-d][1,3]dioxole]-4,4'-dicarbaldehyde

Conditions
ConditionsYield
With zinc(II) chloride In acetonitrile at 60℃; for 5h; Reagent/catalyst; Solvent; Temperature;93.5%
1.3-propanedithiol
109-80-8

1.3-propanedithiol

(rac)-gossypol
303-45-7

(rac)-gossypol

8,8'-bis-[1,3]dithian-2-yl-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

8,8'-bis-[1,3]dithian-2-yl-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

Conditions
ConditionsYield
Stage #1: 1.3-propanedithiol; (rac)-gossypol In chloroform at 20℃; for 1h;
Stage #2: With boron trifluoride diethyl etherate In chloroform at 20℃; for 15h;
93%
glucosamine
14257-69-3

glucosamine

(rac)-gossypol
303-45-7

(rac)-gossypol

C36H41NO12

C36H41NO12

Conditions
ConditionsYield
In methanol at 20℃; for 3h; Inert atmosphere;92.9%
Conditions
ConditionsYield
In methanol at 20℃; for 3h; Inert atmosphere;92.6%
p-Aminohippuric acid
61-78-9

p-Aminohippuric acid

(rac)-gossypol
303-45-7

(rac)-gossypol

(4-{[8'-[1-[4-(Carboxymethyl-carbamoyl)-phenylamino]-meth-(Z)-ylidene]-1,6,1',6'-tetrahydroxy-5,5'-diisopropyl-3,3'-dimethyl-7,7'-dioxo-7',8'-dihydro-7H-[2,2']binaphthalenyl-(8Z)-ylidenemethyl]-amino}-benzoylamino)-acetic acid

(4-{[8'-[1-[4-(Carboxymethyl-carbamoyl)-phenylamino]-meth-(Z)-ylidene]-1,6,1',6'-tetrahydroxy-5,5'-diisopropyl-3,3'-dimethyl-7,7'-dioxo-7',8'-dihydro-7H-[2,2']binaphthalenyl-(8Z)-ylidenemethyl]-amino}-benzoylamino)-acetic acid

Conditions
ConditionsYield
With acid In ethanol for 3h; Heating;92.3%
propylamine
107-10-8

propylamine

(rac)-gossypol
303-45-7

(rac)-gossypol

5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-[(E)-propyliminomethyl]-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-[(E)-propyliminomethyl]-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

Conditions
ConditionsYield
In diethyl ether; isopropyl alcohol at 20 - 45℃; for 2.08333h; Condensation;92%
2-phenylpropylamine
582-22-9

2-phenylpropylamine

(rac)-gossypol
303-45-7

(rac)-gossypol

5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-{[(E)-2-phenyl-propylimino]-methyl}-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-{[(E)-2-phenyl-propylimino]-methyl}-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

Conditions
ConditionsYield
In diethyl ether; isopropyl alcohol at 20 - 45℃; for 2.08333h; Condensation;92%
(rac)-gossypol
303-45-7

(rac)-gossypol

pentafluorophenyl hydrazine
828-73-9

pentafluorophenyl hydrazine

5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-(pentafluorophenyl-hydrazonomethyl)-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-(pentafluorophenyl-hydrazonomethyl)-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

Conditions
ConditionsYield
In ethanol for 3h; Heating;91.9%
(rac)-gossypol
303-45-7

(rac)-gossypol

N-Aminoanabasine
86133-36-0

N-Aminoanabasine

5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-{[(Z)-3,4,5,6-tetrahydro-2H-[2,3']bipyridinyl-1-ylimino]-methyl}-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol
86133-35-9

5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-{[(Z)-3,4,5,6-tetrahydro-2H-[2,3']bipyridinyl-1-ylimino]-methyl}-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

Conditions
ConditionsYield
In ethanol Heating;91%
n-Dodecylamine
124-22-1

n-Dodecylamine

(rac)-gossypol
303-45-7

(rac)-gossypol

1,6,7,1',6',7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthyl-8,8'-dicarbaldehyde bis-dodecylimine
5463-57-0

1,6,7,1',6',7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthyl-8,8'-dicarbaldehyde bis-dodecylimine

Conditions
ConditionsYield
In diethyl ether; isopropyl alcohol at 20 - 45℃; for 2.08333h; Condensation;91%
(rac)-gossypol
303-45-7

(rac)-gossypol

gossypolone
4547-72-2

gossypolone

Conditions
ConditionsYield
Stage #1: (rac)-gossypol With iron(III) chloride; acetic acid In water; acetone at 100℃; for 2h;
Stage #2: With sulfuric acid In diethyl ether; water
91%
With iron(III) chloride In acetic acid; acetone at 60 - 70℃; Oxidation;49%
With iron(III) chloride; acetic acid In acetone at 70℃; for 0.75h;
(rac)-gossypol
303-45-7

(rac)-gossypol

C7H10N2O5(2-)*2Na(1+)

C7H10N2O5(2-)*2Na(1+)

C37H38N2O12(2-)*2Na(1+)

C37H38N2O12(2-)*2Na(1+)

Conditions
ConditionsYield
With sodium hydroxide In methanol at 20℃; for 3h; pH=7.4; Inert atmosphere;90.8%
4-aminophthalimide
3676-85-5

4-aminophthalimide

(rac)-gossypol
303-45-7

(rac)-gossypol

gossypolydenebis-N-(3-iminophthalimide)

gossypolydenebis-N-(3-iminophthalimide)

Conditions
ConditionsYield
In ethanol for 3h; Heating;90.17%
4'-aminobenzo-15-crown-5-ether
60835-71-4

4'-aminobenzo-15-crown-5-ether

(rac)-gossypol
303-45-7

(rac)-gossypol

1,6,1',6'-tetrahydroxy-5,5'-diisopropyl-3,3'-dimethyl-8,8'-bis-[(6,7,9,10,12,13,15,16-octahydro-5,8,11,14,17-pentaoxa-benzocyclopentadecen-2-ylamino)-methylene]-8H,8'H-[2,2']binaphthalenyl-7,7'-dione

1,6,1',6'-tetrahydroxy-5,5'-diisopropyl-3,3'-dimethyl-8,8'-bis-[(6,7,9,10,12,13,15,16-octahydro-5,8,11,14,17-pentaoxa-benzocyclopentadecen-2-ylamino)-methylene]-8H,8'H-[2,2']binaphthalenyl-7,7'-dione

Conditions
ConditionsYield
In ethanol for 6h; Heating;90.1%
4-(3-Aminopropyl)morpholine
123-00-2

4-(3-Aminopropyl)morpholine

(rac)-gossypol
303-45-7

(rac)-gossypol

5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-{[(Z)-3-morpholin-4-yl-propylimino]-methyl}-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol
104757-46-2

5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-{[(Z)-3-morpholin-4-yl-propylimino]-methyl}-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

Conditions
ConditionsYield
In isopropyl alcohol Heating;90%
(rac)-gossypol
303-45-7

(rac)-gossypol

isobutylamine
78-81-9

isobutylamine

8,8'-Bis-[(E)-isobutylimino-methyl]-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

8,8'-Bis-[(E)-isobutylimino-methyl]-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

Conditions
ConditionsYield
In diethyl ether; isopropyl alcohol at 20 - 45℃; for 2.08333h; Condensation;90%
(rac)-gossypol
303-45-7

(rac)-gossypol

N-butylamine
109-73-9

N-butylamine

GSBN

GSBN

Conditions
ConditionsYield
In diethyl ether; isopropyl alcohol at 20 - 45℃; for 2.08333h; Condensation;90%

303-45-7Relevant articles and documents

1H AND 13C NMR SPECTRA OF TRANSFORMATION PRODUCTS OF GOSSYPOL IN SOLUTIONS

Abdullaev, N. D.,Tyshchenko, A. A.,Nazarova, I. P.,Ul'chenko, N. T.,Yagudaev, M. R.,Glushenkova, A. I.

, p. 129 - 138 (1990)

The complete cycle of the transformation of gossypol in solutions takes place in the measuring ampul of a NMR spectrometer.It has been established for the first time that, in methanol, gossypol is converted into stereoisomeric dilactol 15,15'-dimethyl ethers which change into dianhydrogossypol in chloroform and back into gossypol in aqueous acetone.The 1H and 13C NMR spectra of the main and intermediate products of the conversion of gossypol in the solvents mentioned have been studied in detail for the first time and a complete assignment of their resonance characteristics has been made.It has been shown that dianhydrogossypol is formed through intermediate stereoisomeric 15,15'-dimethyl ethers of the dilactol form of gossypol.

Veech et al.

, p. 144 (1976)

A regioselective route to gossypol analogues: The synthesis of gossypol and 5,5'-didesisopropyl-5,5'-diethylgossypol

Meltzer,Bickford,Lambert

, p. 3121 - 3124 (1985)

-

Preparation method and intermediate of gossypol and derivative thereof

-

, (2020/11/12)

The invention discloses a preparation method and an intermediate of gossypol and derivatives thereof. The preparation method comprises the following steps: in a solvent, under the action of alkali, apalladium catalyst and a chiral ligand, carrying out a coupling reaction shown in the specification on a compound 6 and a double-boron reagent to obtain a compound (+)-7, wherein the structure of thechiral ligand is shown as a formula L1. The preparation method is simple, easy to operate and suitable for industrial production.

Method for preparing free gossypol by using gossypol acetate as raw material

-

Paragraph 0041-0076, (2018/07/30)

The invention relates to a method for preparing free gossypol by using gossypol acetate as a raw material. According to the method, an intermolecular hydrogen bond between acetic acid and gossypol inthe gossypol acetate is destroyed by means of ultrasonic waves, and then the acetic acid is enabled to enter an aqueous solution or a saturated saline solution, so that the free gossypol is separatedfrom the acetic acid; the crude free gossypol is enabled to be subjected to recrystallization so as to obtain the high purity free gossypol; the whole preparation process is carried out at the room temperature, and the preparation time is short, so that the oxidation of a gossypol structure and the conversion between various isomers are effectively avoided; the method is low in raw material cost,short in process flow, good in repeatability, high in purity and safety, short in time and high in efficiency, and has certain economic value and practical value.

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