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66575-29-9

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  • 1H-Naphtho[2,1-b]pyran-1-one,5-(acetyloxy)-3-ethenyldodecahydro-6,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-,(3R,4aR,5S,6S,6aS,10S,10aR,10bS)- Manufacturer/High quality/Best price/In stock

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  • Titanium dioxide CAS NO.13463-67-7COLEUS FORSKOHLII EXTRACT ( FORSKOLIN 10-95% ) -Weight Management CAS NO.66575-29-9

    Cas No: 66575-29-9

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66575-29-9 Usage

Description

Forskolin (66575-29-9) is a widely used adenylate cyclase activator.1 Forskolin also is a positive inotropic agent, vasodilator and induces platelet activation among other activities.2-5

Uses

Different sources of media describe the Uses of 66575-29-9 differently. You can refer to the following data:
1. Forskolin is a diterpene isolated from Coleus forskohlii, possessing vasodilating and cardiostimulatory properties. Forskolin resensitizes cell receptors by activating the enzyme adenylyl cyclase and increasing the intracellular levels of cAMP.
2. adenylate cyclase activator, antiglaucoma, hypotensive, vasodilator
3. Cyclic AMP (cAMP) is an important signal carrier necessary for the proper biological response of cells to hormones, neurotransmitters, and other extracellular signals Forskolin is a naturally occurring diterpene that is produced by the Indian Coleus plant (C. forskohlii). It directly activates adenylyl cyclase through its catalytic subunit and is commonly used to raise levels of cAMP in a wide variety of intact cells and tissue preparations. Forskolin binds to adenylyl cyclase in membranes from stably transfected Sf9 cells expressing type 1 adenylyl cyclase with an IC50 value of 41 nM and demonstrates an EC50 value of 0.5 μM in an activation assay assessing formation of cAMP from ATP. Forskolin also interacts with glucose transporters and certain ion channels and has been used for examining adenylyl cyclase expression, regulation, and G protein signaling.[Cayman Chemical]
4. An adenylate cyclase activator and MAP kinase inhibitor
5. In purification of adenylate cyclase.

General Description

Forskolin, present predominantly in the root of Coleus forskohlii plant, is a potential pharmacological compound. It is used for treating hypertension, respiratory disorders and obesity. Forskolin is a diterpenoid capable of modulating adenylate cyclase enzyme and cyclic adenosine monophosphate (cAMP) levels. Engineering forskolin biosynthetic pathway caters its commercial production for pharmacological use. Forskolin has antioxidant and anti-inflammatory property and reduces hyperglycemia by stimulating insulin release. Forskolin promotes differentiation of hepatoma HepaRG cells and activates farnesoid X receptor (FXR) and pregnane X receptor(PXR).

Biological Activity

Cell-permeable activator of adenylyl cyclase. Hypotensive and vasodilatory agent. Induces neuronal differentiation in stem cells and in several neuroblastoma. Also available as part of the PKA Tocriset? .

Biochem/physiol Actions

Cell permeable: yes

Purification Methods

It is an antihypertensive, a positive ionotropic, a platelet aggregation inhibitor, and it has adenylate cyclase activating properties [Chem Abstr 89 244150 1978, de Souza et al. Med Res Rev 3 201 1983, X-ray: Tandon et al. Indian J Chem 15B 880 1977]. [Beilstein 18/5 V 55.]

References

1) Awad et al (1983) Interactions of forskolin and adenylate cyclase; J. Biol. Chem., 258 2960 2) Bhat et al (1983) The antihypertensive and positive inotropic diterpene forskolin: effects of structural modifications on its activity; J. Med. Chem., 26 486 3) de Souza et al. (1983) Forskolin: a labdane diterpenoid with antihypertensive, positive inotropic, platelet aggregation inhibitory, and adenylate cyclase activating properties; Med. Res. Rev. 3 201 4) Aylwin & White (1992) Forskolin acts as a noncompetitive inhibitor of nicotinic acetylcholine receptors; Mol. Pharmacol. 41 908 5) Insel & Ostrom (2003) Forskolin as a tool for examining adenylyl cyclase expression, regulation, and G protein signaling; Cell Mol. Neurobiol., 23 305

Check Digit Verification of cas no

The CAS Registry Mumber 66575-29-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,6,5,7 and 5 respectively; the second part has 2 digits, 2 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 66575-29:
(7*6)+(6*6)+(5*5)+(4*7)+(3*5)+(2*2)+(1*9)=159
159 % 10 = 9
So 66575-29-9 is a valid CAS Registry Number.
InChI:InChI=1/C22H34O7/c1-8-19(5)11-14(25)22(27)20(6)13(24)9-10-18(3,4)16(20)15(26)17(28-12(2)23)21(22,7)29-19/h8,13,15-17,24,26-27H,1,9-11H2,2-7H3/t13-,15-,16?,17-,19-,20-,21+,22-/m0/s1

66575-29-9 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Detail
  • TCI America

  • (F0855)  Forskolin  >95.0%(HPLC)

  • 66575-29-9

  • 10mg

  • 950.00CNY

  • Detail
  • TCI America

  • (F0855)  Forskolin  >95.0%(HPLC)

  • 66575-29-9

  • 50mg

  • 2,980.00CNY

  • Detail
  • USP

  • (1283244)  Forskolin  United States Pharmacopeia (USP) Reference Standard

  • 66575-29-9

  • 1283244-40MG

  • 8,447.40CNY

  • Detail
  • Sigma-Aldrich

  • (93049)  Forskolin  analytical standard

  • 66575-29-9

  • 93049-10MG

  • 2,300.22CNY

  • Detail
  • Sigma

  • (F6886)  Forskolin  from Coleus forskohlii, ≥98% (HPLC), powder

  • 66575-29-9

  • F6886-10MG

  • 2,065.05CNY

  • Detail
  • Sigma

  • (F6886)  Forskolin  from Coleus forskohlii, ≥98% (HPLC), powder

  • 66575-29-9

  • F6886-25MG

  • 4,692.87CNY

  • Detail
  • Sigma

  • (F6886)  Forskolin  from Coleus forskohlii, ≥98% (HPLC), powder

  • 66575-29-9

  • F6886-50MG

  • 8,032.05CNY

  • Detail
  • Sigma

  • (F3917)  Forskolin  For use in molecular biology applications

  • 66575-29-9

  • F3917-10MG

  • 2,409.03CNY

  • Detail
  • Sigma

  • (F3917)  Forskolin  For use in molecular biology applications

  • 66575-29-9

  • F3917-25MG

  • 5,208.84CNY

  • Detail

66575-29-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name FORSKOLIN

1.2 Other means of identification

Product number -
Other names 7β-Acetoxy-8,13-epoxy-1α,6β,9α-trihydroxylabd-14-en-11-one

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:66575-29-9 SDS

66575-29-9Synthetic route

acetic anhydride
108-24-7

acetic anhydride

7-deacetyl forskolin
64657-20-1

7-deacetyl forskolin

forskolin
66575-29-9

forskolin

Conditions
ConditionsYield
In pyridine at 0℃; for 18h;100%
With pyridine at 0 - 20℃; for 18h;100%
With pyridine at 0℃; for 20h;83%
(13R)-Spiroforskolin
220423-84-7

(13R)-Spiroforskolin

forskolin
66575-29-9

forskolin

Conditions
ConditionsYield
In methanol for 96h;
7-deacetyl forskolin
64657-20-1

7-deacetyl forskolin

acetyl chloride
75-36-5

acetyl chloride

A

(3R,4aR,5S,6S,6aS,10S,10aR,10bS)-6-(acetyloxy)-3-ethenyldodecahydro-5,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1H-naphtho[2,1-b]pyran-1-one
64657-21-2

(3R,4aR,5S,6S,6aS,10S,10aR,10bS)-6-(acetyloxy)-3-ethenyldodecahydro-5,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1H-naphtho[2,1-b]pyran-1-one

B

forskolin
66575-29-9

forskolin

C

1-acetyl-7-deacetylforskolin

1-acetyl-7-deacetylforskolin

Conditions
ConditionsYield
With diisopropylamine In toluene for 3h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane for 3h; Ambient temperature; Yield given. Yields of byproduct given;
(1S,6S,12S,16S,2R)-14-hydroxy-4,4,7,9,13,17,17-heptamethyl-3,5,8-trioxa-9-vinyltetracyclo[11.4.0.0.2,607,12]heptadecan-11-one
898546-13-9

(1S,6S,12S,16S,2R)-14-hydroxy-4,4,7,9,13,17,17-heptamethyl-3,5,8-trioxa-9-vinyltetracyclo[11.4.0.0.2,607,12]heptadecan-11-one

forskolin
66575-29-9

forskolin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 100 percent / sodium / 2-methyl-propan-2-ol / 29 h / 30 °C
2: 100 percent / aqueous hydrochloric acid / tetrahydrofuran / 1 h / 20 °C
3: 96 percent / potassium hydride / tetrahydrofuran / 0.13 h / 20 °C
4: 61 percent / potassium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C
5: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C
6: 100 percent / pyridine / 18 h / 0 °C
View Scheme
(2S,7S,13S,14S,6R,9R)-14-hydroxy-4,4,7,9,13,17,17-heptamethyl-3,5,8-trioxa-9-vinyltetracyclo[11.4.0.02,607,12]heptadec-11-one
93108-68-0

(2S,7S,13S,14S,6R,9R)-14-hydroxy-4,4,7,9,13,17,17-heptamethyl-3,5,8-trioxa-9-vinyltetracyclo[11.4.0.02,607,12]heptadec-11-one

forskolin
66575-29-9

forskolin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 96 percent / potassium hydride / tetrahydrofuran / 0.13 h / 20 °C
2: 61 percent / potassium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C
3: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C
4: 100 percent / pyridine / 18 h / 0 °C
View Scheme
(1S,6S,12S,16S,2R,11R)-14-methoxy-1,4,4,8,8,12,16-heptamethyl-3,5,17-trioxa-16-vinyltetracyclo[11.4.0.0.2,607,12]heptadec-14-en-11-ol
898546-12-8

(1S,6S,12S,16S,2R,11R)-14-methoxy-1,4,4,8,8,12,16-heptamethyl-3,5,17-trioxa-16-vinyltetracyclo[11.4.0.0.2,607,12]heptadec-14-en-11-ol

forskolin
66575-29-9

forskolin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 80 percent / pyridine; chromium oxide / CH2Cl2 / 24 h / 20 °C
2: 100 percent / sodium / 2-methyl-propan-2-ol / 29 h / 30 °C
3: 100 percent / aqueous hydrochloric acid / tetrahydrofuran / 1 h / 20 °C
4: 96 percent / potassium hydride / tetrahydrofuran / 0.13 h / 20 °C
5: 61 percent / potassium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C
6: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C
7: 100 percent / pyridine / 18 h / 0 °C
View Scheme
(1S,6S,11S,12S,2R)-14-methoxy-1,4,4,8,8,12,16-heptamethyl-3,5,17-trioxa-16-vinyltetracyclo[11.4.0.0.2,607,12]heptadec-14-en-11-ol
115155-11-8

(1S,6S,11S,12S,2R)-14-methoxy-1,4,4,8,8,12,16-heptamethyl-3,5,17-trioxa-16-vinyltetracyclo[11.4.0.0.2,607,12]heptadec-14-en-11-ol

forskolin
66575-29-9

forskolin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 100 percent / aqueous hydrochloric acid / tetrahydrofuran / 1 h / 20 °C
2: 96 percent / potassium hydride / tetrahydrofuran / 0.13 h / 20 °C
3: 61 percent / potassium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C
4: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C
5: 100 percent / pyridine / 18 h / 0 °C
View Scheme
(1S,6S,11S,12S,2R,16R)-14-methoxy-1,4,4,8,8,12,16-heptamethyl-3,5,17-trioxa-16-vinyltetracyclo[11.4.0.02,607,12]heptadec-13-en-11-ol
115155-09-4

(1S,6S,11S,12S,2R,16R)-14-methoxy-1,4,4,8,8,12,16-heptamethyl-3,5,17-trioxa-16-vinyltetracyclo[11.4.0.02,607,12]heptadec-13-en-11-ol

forskolin
66575-29-9

forskolin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 61 percent / potassium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C
2: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C
3: 100 percent / pyridine / 18 h / 0 °C
View Scheme
(6S,11S,16S,1R,2R,12R,13R)-14-methoxy-1,4,4,8,8,12,16-heptamethyl-3,5,17-trioxa-16-vinyltetracyclo[11.4.0.0.2,607,12]heptadec-14-en-11,13-diol
898546-14-0

(6S,11S,16S,1R,2R,12R,13R)-14-methoxy-1,4,4,8,8,12,16-heptamethyl-3,5,17-trioxa-16-vinyltetracyclo[11.4.0.0.2,607,12]heptadec-14-en-11,13-diol

forskolin
66575-29-9

forskolin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C
2: 100 percent / pyridine / 18 h / 0 °C
View Scheme
(1S,7S,9S,3R,5R,8R,14R)-14-acetyloxy-8,9-dihydroxy-1,5,7,11,11-pentamethyl-6-oxa-5-vinyltricyclo[8.4.0.02,7]tetradec-3-yl acetate
157201-96-2

(1S,7S,9S,3R,5R,8R,14R)-14-acetyloxy-8,9-dihydroxy-1,5,7,11,11-pentamethyl-6-oxa-5-vinyltricyclo[8.4.0.02,7]tetradec-3-yl acetate

forskolin
66575-29-9

forskolin

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 93 percent / p-toluenesulfonic acid / 24 h / 50 °C
2: 96 percent / lithium aluminumhydride / diethyl ether / 2.5 h / 20 °C
3: 89 percent / pyridinium chlorochromate; sodium acetate / CH2Cl2 / 3 h / 20 °C
4: 54 percent / potassium hydride / tetrahydrofuran / 0.5 h / 0 °C
5: 80 percent / pyridine; chromium oxide / CH2Cl2 / 24 h / 20 °C
6: 100 percent / sodium / 2-methyl-propan-2-ol / 29 h / 30 °C
7: 100 percent / aqueous hydrochloric acid / tetrahydrofuran / 1 h / 20 °C
8: 96 percent / potassium hydride / tetrahydrofuran / 0.13 h / 20 °C
9: 61 percent / potassium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C
10: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C
11: 100 percent / pyridine / 18 h / 0 °C
View Scheme
ptychantin A

ptychantin A

forskolin
66575-29-9

forskolin

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: 100 percent / potassium hydroxide / methanol / 13.5 h / 20 °C
2: 93 percent / p-toluenesulfonic acid / 24 h / 50 °C
3: 96 percent / lithium aluminumhydride / diethyl ether / 2.5 h / 20 °C
4: 89 percent / pyridinium chlorochromate; sodium acetate / CH2Cl2 / 3 h / 20 °C
5: 54 percent / potassium hydride / tetrahydrofuran / 0.5 h / 0 °C
6: 80 percent / pyridine; chromium oxide / CH2Cl2 / 24 h / 20 °C
7: 100 percent / sodium / 2-methyl-propan-2-ol / 29 h / 30 °C
8: 100 percent / aqueous hydrochloric acid / tetrahydrofuran / 1 h / 20 °C
9: 96 percent / potassium hydride / tetrahydrofuran / 0.13 h / 20 °C
10: 61 percent / potassium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C
11: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C
12: 100 percent / pyridine / 18 h / 0 °C
View Scheme
ptychantin B

ptychantin B

forskolin
66575-29-9

forskolin

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: 89 percent / potassium hydroxide / methanol / 13.5 h / 20 °C
2: 93 percent / p-toluenesulfonic acid / 24 h / 50 °C
3: 96 percent / lithium aluminumhydride / diethyl ether / 2.5 h / 20 °C
4: 89 percent / pyridinium chlorochromate; sodium acetate / CH2Cl2 / 3 h / 20 °C
5: 54 percent / potassium hydride / tetrahydrofuran / 0.5 h / 0 °C
6: 80 percent / pyridine; chromium oxide / CH2Cl2 / 24 h / 20 °C
7: 100 percent / sodium / 2-methyl-propan-2-ol / 29 h / 30 °C
8: 100 percent / aqueous hydrochloric acid / tetrahydrofuran / 1 h / 20 °C
9: 96 percent / potassium hydride / tetrahydrofuran / 0.13 h / 20 °C
10: 61 percent / potassium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C
11: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C
12: 100 percent / pyridine / 18 h / 0 °C
View Scheme
(2S,7S,13S,6R,9R,14R)-14-hydroxy-4,4,7,9,13,17,17-heptamethyl-3,5,8-trioxa-9-vinyltetracyclo[11.4.0.02,6.07,12]heptadecan-11-one
537038-62-3

(2S,7S,13S,6R,9R,14R)-14-hydroxy-4,4,7,9,13,17,17-heptamethyl-3,5,8-trioxa-9-vinyltetracyclo[11.4.0.02,6.07,12]heptadecan-11-one

forskolin
66575-29-9

forskolin

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 54 percent / potassium hydride / tetrahydrofuran / 0.5 h / 0 °C
2: 80 percent / pyridine; chromium oxide / CH2Cl2 / 24 h / 20 °C
3: 100 percent / sodium / 2-methyl-propan-2-ol / 29 h / 30 °C
4: 100 percent / aqueous hydrochloric acid / tetrahydrofuran / 1 h / 20 °C
5: 96 percent / potassium hydride / tetrahydrofuran / 0.13 h / 20 °C
6: 61 percent / potassium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C
7: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C
8: 100 percent / pyridine / 18 h / 0 °C
View Scheme
(1S,6S,12S,2R,11R,14R,16R)-1,4,4,8,8,12,16-heptamethyl-3,5,17-trioxa-16-vinyltetracyclo[11.4.0.02,6.07,12]heptadecane-11,14-diol
536742-35-5

(1S,6S,12S,2R,11R,14R,16R)-1,4,4,8,8,12,16-heptamethyl-3,5,17-trioxa-16-vinyltetracyclo[11.4.0.02,6.07,12]heptadecane-11,14-diol

forskolin
66575-29-9

forskolin

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 89 percent / pyridinium chlorochromate; sodium acetate / CH2Cl2 / 3 h / 20 °C
2: 54 percent / potassium hydride / tetrahydrofuran / 0.5 h / 0 °C
3: 80 percent / pyridine; chromium oxide / CH2Cl2 / 24 h / 20 °C
4: 100 percent / sodium / 2-methyl-propan-2-ol / 29 h / 30 °C
5: 100 percent / aqueous hydrochloric acid / tetrahydrofuran / 1 h / 20 °C
6: 96 percent / potassium hydride / tetrahydrofuran / 0.13 h / 20 °C
7: 61 percent / potassium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C
8: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C
9: 100 percent / pyridine / 18 h / 0 °C
View Scheme
(2S,7S,13S,6R,9R,11R,14R)-14-acetyloxy-4,4,7,9,13,17,17-heptamethyl-3,5,8-trioxa-9-vinyltetracyclo[11.4.0.02,6.07,12]heptadec-11-yl acetate
536742-34-4

(2S,7S,13S,6R,9R,11R,14R)-14-acetyloxy-4,4,7,9,13,17,17-heptamethyl-3,5,8-trioxa-9-vinyltetracyclo[11.4.0.02,6.07,12]heptadec-11-yl acetate

forskolin
66575-29-9

forskolin

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 96 percent / lithium aluminumhydride / diethyl ether / 2.5 h / 20 °C
2: 89 percent / pyridinium chlorochromate; sodium acetate / CH2Cl2 / 3 h / 20 °C
3: 54 percent / potassium hydride / tetrahydrofuran / 0.5 h / 0 °C
4: 80 percent / pyridine; chromium oxide / CH2Cl2 / 24 h / 20 °C
5: 100 percent / sodium / 2-methyl-propan-2-ol / 29 h / 30 °C
6: 100 percent / aqueous hydrochloric acid / tetrahydrofuran / 1 h / 20 °C
7: 96 percent / potassium hydride / tetrahydrofuran / 0.13 h / 20 °C
8: 61 percent / potassium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C
9: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C
10: 100 percent / pyridine / 18 h / 0 °C
View Scheme
rac-5α<<(tert-Butyl)dimethylsilyl>oxy>-4β-ethinyl-1,4,4a,5,6,7,8,8aα-octahydro-4-hydroxy-3,4aα,8,8-tetramethylnaphthalin-1(4H)-on
123218-03-1, 123218-04-2

rac-5α<<(tert-Butyl)dimethylsilyl>oxy>-4β-ethinyl-1,4,4a,5,6,7,8,8aα-octahydro-4-hydroxy-3,4aα,8,8-tetramethylnaphthalin-1(4H)-on

A

C22H34O7

C22H34O7

B

forskolin
66575-29-9

forskolin

Conditions
ConditionsYield
Multi-step reaction with 15 steps
1.1: diisobutylaluminium hydride / tetrahydrofuran / 2 h / -78 °C
2.1: dmap / N,N-dimethyl-formamide / 13 h / 65 °C
3.1: pyridinium chlorochromate; sodium acetate / dichloromethane / 72 h / 30 °C / Molecular sieve
4.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / 0 °C
5.1: pyridinium p-toluenesulfonate / dichloromethane / 0.25 h / 23 °C
6.1: triethylamine / chloroform / 1 h / 23 °C
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve
8.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C
9.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C
10.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique
11.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C
12.1: n-butyllithium / hexane / 0.5 h / 23 °C
12.2: 1.17 h / -78 - -30 °C
13.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C
14.1: pyridine / 20 h / 0 °C
15.1: Chiralpak® AD-H / hexane; ethanol / Resolution of racemate
View Scheme
rac-5α<<(tert-Butyl)dimethylsilyl>oxy>-4β-ethinyl-1,4,4a,5,6,7,8,8aα-octahydro-4-hydroxy-3,4aα,8,8-tetramethylnaphthalin-1(4H)-on
123218-03-1, 123218-04-2

rac-5α<<(tert-Butyl)dimethylsilyl>oxy>-4β-ethinyl-1,4,4a,5,6,7,8,8aα-octahydro-4-hydroxy-3,4aα,8,8-tetramethylnaphthalin-1(4H)-on

forskolin
66575-29-9

forskolin

Conditions
ConditionsYield
Multi-step reaction with 17 steps
1.1: diisobutylaluminium hydride / tetrahydrofuran / 2 h / -78 °C
2.1: dmap / N,N-dimethyl-formamide / 13 h / 65 °C
3.1: pyridinium chlorochromate; sodium acetate / dichloromethane / 72 h / 30 °C / Molecular sieve
4.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / 0 °C
5.1: pyridinium p-toluenesulfonate / dichloromethane / 0.25 h / 23 °C
6.1: triethylamine / chloroform / 1 h / 23 °C
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve
8.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C
9.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C
10.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique
11.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C
12.1: n-butyllithium / hexane / 0.5 h / 23 °C
12.2: 1.17 h / -78 - -30 °C
13.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C
14.1: pyridine / 20 h / 0 °C
15.1: dmap; triethylamine / dichloromethane / 1 h / 23 °C
16.1: potassium carbonate / methanol; water / 6 h / 23 °C
17.1: pyridine / 20 h / 0 °C
View Scheme
C22H38O3Si

C22H38O3Si

A

C22H34O7

C22H34O7

B

forskolin
66575-29-9

forskolin

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1.1: dmap / N,N-dimethyl-formamide / 13 h / 65 °C
2.1: pyridinium chlorochromate; sodium acetate / dichloromethane / 72 h / 30 °C / Molecular sieve
3.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / 0 °C
4.1: pyridinium p-toluenesulfonate / dichloromethane / 0.25 h / 23 °C
5.1: triethylamine / chloroform / 1 h / 23 °C
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve
7.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C
8.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C
9.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique
10.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C
11.1: n-butyllithium / hexane / 0.5 h / 23 °C
11.2: 1.17 h / -78 - -30 °C
12.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C
13.1: pyridine / 20 h / 0 °C
14.1: Chiralpak® AD-H / hexane; ethanol / Resolution of racemate
View Scheme
C22H38O3Si

C22H38O3Si

forskolin
66575-29-9

forskolin

Conditions
ConditionsYield
Multi-step reaction with 16 steps
1.1: dmap / N,N-dimethyl-formamide / 13 h / 65 °C
2.1: pyridinium chlorochromate; sodium acetate / dichloromethane / 72 h / 30 °C / Molecular sieve
3.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / 0 °C
4.1: pyridinium p-toluenesulfonate / dichloromethane / 0.25 h / 23 °C
5.1: triethylamine / chloroform / 1 h / 23 °C
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve
7.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C
8.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C
9.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique
10.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C
11.1: n-butyllithium / hexane / 0.5 h / 23 °C
11.2: 1.17 h / -78 - -30 °C
12.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C
13.1: pyridine / 20 h / 0 °C
14.1: dmap; triethylamine / dichloromethane / 1 h / 23 °C
15.1: potassium carbonate / methanol; water / 6 h / 23 °C
16.1: pyridine / 20 h / 0 °C
View Scheme
C29H42O4Si

C29H42O4Si

A

C22H34O7

C22H34O7

B

forskolin
66575-29-9

forskolin

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1.1: pyridinium chlorochromate; sodium acetate / dichloromethane / 72 h / 30 °C / Molecular sieve
2.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / 0 °C
3.1: pyridinium p-toluenesulfonate / dichloromethane / 0.25 h / 23 °C
4.1: triethylamine / chloroform / 1 h / 23 °C
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve
6.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C
7.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C
8.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique
9.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C
10.1: n-butyllithium / hexane / 0.5 h / 23 °C
10.2: 1.17 h / -78 - -30 °C
11.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C
12.1: pyridine / 20 h / 0 °C
13.1: Chiralpak® AD-H / hexane; ethanol / Resolution of racemate
View Scheme
C29H42O4Si

C29H42O4Si

forskolin
66575-29-9

forskolin

Conditions
ConditionsYield
Multi-step reaction with 15 steps
1.1: pyridinium chlorochromate; sodium acetate / dichloromethane / 72 h / 30 °C / Molecular sieve
2.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / 0 °C
3.1: pyridinium p-toluenesulfonate / dichloromethane / 0.25 h / 23 °C
4.1: triethylamine / chloroform / 1 h / 23 °C
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve
6.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C
7.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C
8.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique
9.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C
10.1: n-butyllithium / hexane / 0.5 h / 23 °C
10.2: 1.17 h / -78 - -30 °C
11.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C
12.1: pyridine / 20 h / 0 °C
13.1: dmap; triethylamine / dichloromethane / 1 h / 23 °C
14.1: potassium carbonate / methanol; water / 6 h / 23 °C
15.1: pyridine / 20 h / 0 °C
View Scheme
C29H40O4Si

C29H40O4Si

A

C22H34O7

C22H34O7

B

forskolin
66575-29-9

forskolin

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / 0 °C
2.1: pyridinium p-toluenesulfonate / dichloromethane / 0.25 h / 23 °C
3.1: triethylamine / chloroform / 1 h / 23 °C
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve
5.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C
6.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C
7.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique
8.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C
9.1: n-butyllithium / hexane / 0.5 h / 23 °C
9.2: 1.17 h / -78 - -30 °C
10.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C
11.1: pyridine / 20 h / 0 °C
12.1: Chiralpak® AD-H / hexane; ethanol / Resolution of racemate
View Scheme
C29H40O4Si

C29H40O4Si

forskolin
66575-29-9

forskolin

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / 0 °C
2.1: pyridinium p-toluenesulfonate / dichloromethane / 0.25 h / 23 °C
3.1: triethylamine / chloroform / 1 h / 23 °C
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve
5.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C
6.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C
7.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique
8.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C
9.1: n-butyllithium / hexane / 0.5 h / 23 °C
9.2: 1.17 h / -78 - -30 °C
10.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C
11.1: pyridine / 20 h / 0 °C
12.1: dmap; triethylamine / dichloromethane / 1 h / 23 °C
13.1: potassium carbonate / methanol; water / 6 h / 23 °C
14.1: pyridine / 20 h / 0 °C
View Scheme
C22H38O3Si

C22H38O3Si

A

C22H34O7

C22H34O7

B

forskolin
66575-29-9

forskolin

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: pyridinium p-toluenesulfonate / dichloromethane / 0.25 h / 23 °C
2.1: triethylamine / chloroform / 1 h / 23 °C
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve
4.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C
5.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C
6.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique
7.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C
8.1: n-butyllithium / hexane / 0.5 h / 23 °C
8.2: 1.17 h / -78 - -30 °C
9.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C
10.1: pyridine / 20 h / 0 °C
11.1: Chiralpak® AD-H / hexane; ethanol / Resolution of racemate
View Scheme
C22H38O3Si

C22H38O3Si

forskolin
66575-29-9

forskolin

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1.1: pyridinium p-toluenesulfonate / dichloromethane / 0.25 h / 23 °C
2.1: triethylamine / chloroform / 1 h / 23 °C
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve
4.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C
5.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C
6.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique
7.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C
8.1: n-butyllithium / hexane / 0.5 h / 23 °C
8.2: 1.17 h / -78 - -30 °C
9.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C
10.1: pyridine / 20 h / 0 °C
11.1: dmap; triethylamine / dichloromethane / 1 h / 23 °C
12.1: potassium carbonate / methanol; water / 6 h / 23 °C
13.1: pyridine / 20 h / 0 °C
View Scheme
C25H42O3Si

C25H42O3Si

A

C22H34O7

C22H34O7

B

forskolin
66575-29-9

forskolin

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: triethylamine / chloroform / 1 h / 23 °C
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve
3.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C
4.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C
5.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique
6.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C
7.1: n-butyllithium / hexane / 0.5 h / 23 °C
7.2: 1.17 h / -78 - -30 °C
8.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C
9.1: pyridine / 20 h / 0 °C
10.1: Chiralpak® AD-H / hexane; ethanol / Resolution of racemate
View Scheme
C25H42O3Si

C25H42O3Si

forskolin
66575-29-9

forskolin

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: triethylamine / chloroform / 1 h / 23 °C
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve
3.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C
4.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C
5.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique
6.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C
7.1: n-butyllithium / hexane / 0.5 h / 23 °C
7.2: 1.17 h / -78 - -30 °C
8.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C
9.1: pyridine / 20 h / 0 °C
10.1: dmap; triethylamine / dichloromethane / 1 h / 23 °C
11.1: potassium carbonate / methanol; water / 6 h / 23 °C
12.1: pyridine / 20 h / 0 °C
View Scheme
C27H45NO4Si

C27H45NO4Si

A

C22H34O7

C22H34O7

B

forskolin
66575-29-9

forskolin

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve
2.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C
3.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C
4.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique
5.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C
6.1: n-butyllithium / hexane / 0.5 h / 23 °C
6.2: 1.17 h / -78 - -30 °C
7.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C
8.1: pyridine / 20 h / 0 °C
9.1: Chiralpak® AD-H / hexane; ethanol / Resolution of racemate
View Scheme
C27H45NO4Si

C27H45NO4Si

forskolin
66575-29-9

forskolin

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve
2.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C
3.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C
4.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique
5.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C
6.1: n-butyllithium / hexane / 0.5 h / 23 °C
6.2: 1.17 h / -78 - -30 °C
7.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C
8.1: pyridine / 20 h / 0 °C
9.1: dmap; triethylamine / dichloromethane / 1 h / 23 °C
10.1: potassium carbonate / methanol; water / 6 h / 23 °C
11.1: pyridine / 20 h / 0 °C
View Scheme
forskolin
66575-29-9

forskolin

1,1'-Thiocarbonyldiimidazole
6160-65-2

1,1'-Thiocarbonyldiimidazole

C23H32O7S

C23H32O7S

Conditions
ConditionsYield
With dmap In dichloromethane at 20℃; for 4h; Inert atmosphere;97%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

forskolin
66575-29-9

forskolin

1-(trimethylsilyl)forskolin
84010-19-5

1-(trimethylsilyl)forskolin

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 22℃; for 2h; Inert atmosphere;92%
With pyridine; 1,1,1,3,3,3-hexamethyl-disilazane at 80 - 85℃; for 2h;77%
p-methoxybenzyloxy acetic acid
88920-24-5

p-methoxybenzyloxy acetic acid

forskolin
66575-29-9

forskolin

7β-acetoxy-6β,9α-dihydroxy-8,13-epoxy-1α-<(4-methoxybenzyloxy)acetoxy>labd-14-en-11-one
120370-89-0

7β-acetoxy-6β,9α-dihydroxy-8,13-epoxy-1α-<(4-methoxybenzyloxy)acetoxy>labd-14-en-11-one

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In ethyl acetate for 3h; Ambient temperature;92%
forskolin
66575-29-9

forskolin

2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

C25H38O7
119603-26-8

C25H38O7

Conditions
ConditionsYield
With toluene-4-sulfonic acid In acetone at 0 - 20℃; for 6h; Inert atmosphere;92%
triethyl borane
97-94-9

triethyl borane

forskolin
66575-29-9

forskolin

ethyl iodoacetae
623-48-3

ethyl iodoacetae

C28H45BO9

C28H45BO9

Conditions
ConditionsYield
With 4-tert-Butylcatechol; sodium hydrogencarbonate In dichloromethane; benzene at 20℃; for 3h; Darkness;91%
forskolin
66575-29-9

forskolin

14,15-dihydroforskolin
64657-24-5

14,15-dihydroforskolin

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃;90%
palladium-carbon In methanol
forskolin
66575-29-9

forskolin

1-deoxy-1-oxoforskolin
81873-10-1

1-deoxy-1-oxoforskolin

Conditions
ConditionsYield
With 4-methyl-morpholine; 6C13H13P*4CF3O3S(1-)*2Ru(2+); acetone at 65℃; for 3h; Inert atmosphere; Sealed tube;88%
With Collins oxidation agent In dichloromethane for 2.5h;1.2 g
forskolin
66575-29-9

forskolin

allyl alcohol
107-18-6

allyl alcohol

1,9-O-[(3-allyloxy)propylidene]forskolin

1,9-O-[(3-allyloxy)propylidene]forskolin

Conditions
ConditionsYield
With ammonium cerium (IV) nitrate In acetonitrile at 20℃; for 24h; Inert atmosphere; regioselective reaction;87%
phosgene
75-44-5

phosgene

forskolin
66575-29-9

forskolin

forskolin 1,9-carbonate
81826-81-5

forskolin 1,9-carbonate

Conditions
ConditionsYield
With pyridine In toluene at 0 - 20℃; for 4.5h;86%
With pyridine In toluene at 0℃; for 1h;1.22 g
4-[(dimethylamino)methyl]benzoic acid hydrochloride

4-[(dimethylamino)methyl]benzoic acid hydrochloride

forskolin
66575-29-9

forskolin

7β-acetoxy-6β,9α-dihydroxy-1α-(4-dimethylaminomethylbenzoyloxy)-8,13-epoxy-labd-14-en-11-one hydrochloride

7β-acetoxy-6β,9α-dihydroxy-1α-(4-dimethylaminomethylbenzoyloxy)-8,13-epoxy-labd-14-en-11-one hydrochloride

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide for 16h;82.3%
forskolin
66575-29-9

forskolin

7-deacetyl forskolin
64657-20-1

7-deacetyl forskolin

Conditions
ConditionsYield
With ethylenediamine In methanol for 0.0833333h; Microwave irradiation;80%
With sodium hydroxide In methanol; water
With potassium carbonate In methanol at 25℃; for 0.75h;
With water first-order plots of degradation in water and phosphate buffer (pH 6.0-8.0);
In methanol; potassium carbonate
forskolin
66575-29-9

forskolin

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

7β-acetoxy-1α-<(tert-butyldimethylsilyl)oxy>-6β,9α-dihydroxy-8,13-epoxylabd-14-en-11-one
105559-76-0

7β-acetoxy-1α-<(tert-butyldimethylsilyl)oxy>-6β,9α-dihydroxy-8,13-epoxylabd-14-en-11-one

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 70℃; for 22h;80%
forskolin
66575-29-9

forskolin

1-(prop-2-yn-1-yl)-1H-indole-3-carbaldehyde

1-(prop-2-yn-1-yl)-1H-indole-3-carbaldehyde

1,9-O-(N-propargyl-3-indolylidene)forskolin

1,9-O-(N-propargyl-3-indolylidene)forskolin

Conditions
ConditionsYield
With Amberlist-15 wet In 1,2-dichloro-ethane at 20℃; for 24h;75%
forskolin
66575-29-9

forskolin

acetone
67-64-1

acetone

C25H38O7
119603-26-8

C25H38O7

Conditions
ConditionsYield
With aluminium trichloride In diethyl ether for 0.3h; Ambient temperature;74%
forskolin
66575-29-9

forskolin

benzoyl chloride
98-88-4

benzoyl chloride

1-benzoylforskolin
84048-17-9

1-benzoylforskolin

Conditions
ConditionsYield
With pyridine Ambient temperature;72%
forskolin
66575-29-9

forskolin

acetyl chloride
75-36-5

acetyl chloride

Acetic acid (3S,4aR,5S,6S,6aS,10S,10aR,10bS)-5-acetoxy-3-ethyl-6,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-dodecahydro-benzo[f]chromen-10-yl ester
84010-29-7

Acetic acid (3S,4aR,5S,6S,6aS,10S,10aR,10bS)-5-acetoxy-3-ethyl-6,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-dodecahydro-benzo[f]chromen-10-yl ester

Conditions
ConditionsYield
With pyridine Ambient temperature;72%
triethyl borane
97-94-9

triethyl borane

((Iodomethyl)sulfonyl)benzene
65492-21-9

((Iodomethyl)sulfonyl)benzene

forskolin
66575-29-9

forskolin

C31H45BO9S

C31H45BO9S

Conditions
ConditionsYield
With 4-tert-Butylcatechol; sodium hydrogencarbonate In dichloromethane; benzene at 20℃; for 3h; Darkness;63%
pivaloyl chloride
3282-30-2

pivaloyl chloride

forskolin
66575-29-9

forskolin

7-deacetyl-1,7-dipivaloylforskolin
84010-28-6

7-deacetyl-1,7-dipivaloylforskolin

Conditions
ConditionsYield
With pyridine Ambient temperature;55%
forskolin
66575-29-9

forskolin

benzoyl chloride
98-88-4

benzoyl chloride

C34H40O8
84048-21-5

C34H40O8

Conditions
ConditionsYield
With pyridine Ambient temperature;55%
forskolin
66575-29-9

forskolin

forskolin-14,15-dibromide
84010-25-3

forskolin-14,15-dibromide

Conditions
ConditionsYield
With bromine In carbon disulfide at 0 - 20℃; for 2.75h;50%
forskolin
66575-29-9

forskolin

phenyl isocyanate
103-71-9

phenyl isocyanate

1-(anilinocarbonyl)forskolin
84048-18-0

1-(anilinocarbonyl)forskolin

Conditions
ConditionsYield
In toluene for 20h; Heating;48%
forskolin
66575-29-9

forskolin

(13R)-Spiroforskolin
220423-84-7

(13R)-Spiroforskolin

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In benzene at 0 - 5℃;45%
forskolin
66575-29-9

forskolin

benzoic acid
65-85-0

benzoic acid

1β-Benzoyloxy-1-deoxycoleonol
132620-05-4

1β-Benzoyloxy-1-deoxycoleonol

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran for 36h; Ambient temperature;45%
forskolin
66575-29-9

forskolin

A

7β-acetoxy-8,13-epoxy-6β-hydroxy-11-oxolabd-14-ene-1α,9α-diyl cyclo-α-phosphite
144426-70-0, 144539-48-0

7β-acetoxy-8,13-epoxy-6β-hydroxy-11-oxolabd-14-ene-1α,9α-diyl cyclo-α-phosphite

B

7β-acetoxy-8,13-epoxy-6β-hydroxy-11-oxolabd-14-ene-1α,9α-diyl cyclo-β-phosphite
144426-70-0, 144539-48-0

7β-acetoxy-8,13-epoxy-6β-hydroxy-11-oxolabd-14-ene-1α,9α-diyl cyclo-β-phosphite

Conditions
ConditionsYield
With pyridine; bis(trifluoroethyl)hydrogen phosphite for 16h; Ambient temperature;A 39%
B 13%
forskolin
66575-29-9

forskolin

propargyl bromide
106-96-7

propargyl bromide

A

1-O-propargyl-forskolin
1350721-63-9

1-O-propargyl-forskolin

B

1-O-propargyl-6-O-acetyl-7-deacetyl-forskolin
1350721-66-2

1-O-propargyl-6-O-acetyl-7-deacetyl-forskolin

Conditions
ConditionsYield
With potassium carbonate; sodium iodide In acetone at 20℃; Reflux;A 36%
B 35%
With potassium carbonate; potassium iodide In acetone for 24h; Reflux;A 1.8 g
B 1.7 g
forskolin
66575-29-9

forskolin

A

7β-acetoxy-8,13-epoxy-6β-hydroxy-11-oxolabd-14-ene-1α,9α-diyl cyclophospho-α-chloridate
144426-66-4, 144491-36-1

7β-acetoxy-8,13-epoxy-6β-hydroxy-11-oxolabd-14-ene-1α,9α-diyl cyclophospho-α-chloridate

B

7β-acetoxy-8,13-epoxy-6β-hydroxy-11-oxolabd-14-ene-1α,9α-diyl cyclophospho-β-chloridate
144426-66-4, 144491-36-1

7β-acetoxy-8,13-epoxy-6β-hydroxy-11-oxolabd-14-ene-1α,9α-diyl cyclophospho-β-chloridate

Conditions
ConditionsYield
With pyridine; triethylamine; trichlorophosphate In diethyl ether 1) -10 deg C, 1 h, 2) RT, 60 h; other substrate, various phosphorylating agents;A 33%
B 12%
With pyridine; triethylamine; trichlorophosphate In diethyl ether 1) -10 deg C, 1 h, 2) RT, 60 h;A 33%
B 12%
forskolin
66575-29-9

forskolin

3,5-dinitrobenoyl chloride
99-33-2

3,5-dinitrobenoyl chloride

6β-acetoxy-7β-(3,5-dinitro)benzoyloxy-8,13-epoxy-1α,9-dihydroxy-labd-14-en-11-one

6β-acetoxy-7β-(3,5-dinitro)benzoyloxy-8,13-epoxy-1α,9-dihydroxy-labd-14-en-11-one

Conditions
ConditionsYield
With pyridine at 20℃; for 1.5h;31%
forskolin
66575-29-9

forskolin

7β-acetoxy-8,13-epoxy-6β,9α-dihydroxy-11-oxolabd-14-en-1α-yl dihydrogen phosphate
144426-76-6

7β-acetoxy-8,13-epoxy-6β,9α-dihydroxy-11-oxolabd-14-en-1α-yl dihydrogen phosphate

Conditions
ConditionsYield
With dihydro-(1,2-dibromo-2-phenyl-1-ethyl)phosphonic acid; N-ethyl-N,N-diisopropylamine In dichloromethane for 48h; Ambient temperature;30%

66575-29-9Relevant articles and documents

A Radical-Polar Crossover Annulation to Access Terpenoid Motifs

Thomas, William P.,Schatz, Devon J.,George, David T.,Pronin, Sergey V.

supporting information, p. 12246 - 12250 (2019/08/27)

A new catalytic radical-polar crossover annulation between two unsaturated carbonyl compounds is described. The annulation proceeds under exceptionally mild conditions and provides direct and expedient access to complex terpenoid motifs. Application of this chemistry allows for synthesis of forskolin, a densely functionalized terpenoid, in 14 steps from commercially available material.

Expedient synthetic transformation of ptychantins into Forskolin

Hagiwara, Hisahiro,Tsukagoshi, Masashi,Hoshi, Takashi,Suzuki, Toshio,Hashimoto, Toshihiro,Asakawa, Yoshinori

, p. 929 - 931 (2008/12/22)

Forskolin has been synthesized in 11 steps with a 17% overall yield from ptychantins A and B, which have been isolated from the liverwort Ptychanthus striatus in good yield. The 1α-hydroxy group was furnished by stereoselective reduction of the corresponding carbonyl group by sodium cyanoborohydride. The 9α-hydroxy group was introduced stereoselectively by epoxidation of Δ9,11-enol ether. Georg Thieme Verlag Stuttgart.

Total synthesis of forskolin - Part II

Delpech, Bernard,Calvo, Daniel,Lett, Robert

, p. 1019 - 1022 (2007/10/03)

The further elaboration of the key-intermediate 5 into forskolin 1 has been achieved via two different routes. Key features of this new total synthesis are: 1) the stereospecific formation of the 6β, 7β, 8α-triol via the BF3-Et2O assisted opening of the epoxy carbamate 8; 2) use of the 8α, 11-di-t-butylsilylene ketal for the specific protection of the 6β, 7β-diol, from the tetrol 10(A); two new sequences for the formation of the dihydro-γ-pyrone ring in high overall yield from 23; 4) the stereoselective divinyl cuprate conjugate α-addition on the dihydro-γ-pyrone 16 or 28, in the presence of BF3-Et2o, with the stereochemistry required for forskolin synthesis.

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