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1944-63-4

1944-63-4

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1944-63-4 Usage

Uses

1,5-Dioxo-7aβ-methyl-3aα-hexahydroindane-4α-propionic Acid, can be used for the novel and concise synthesis of 19-Nor-10-azasteroids, a new class of steroid 5α-reductase inhibitors.

Check Digit Verification of cas no

The CAS Registry Mumber 1944-63-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,9,4 and 4 respectively; the second part has 2 digits, 6 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 1944-63:
(6*1)+(5*9)+(4*4)+(3*4)+(2*6)+(1*3)=94
94 % 10 = 4
So 1944-63-4 is a valid CAS Registry Number.

1944-63-4SDS

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 3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-2,3,3a,4,6,7-hexahydroinden-4-yl]propanoic acid

1.2 Other means of identification

Product number -
Other names 9,17-Dioxo-1,2,3,4,10,19-hexanorandrostan-5-oic acid

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:1944-63-4 SDS

1944-63-4Synthetic route

C13H18O3

C13H18O3

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1944-63-4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione

Conditions
ConditionsYield
With sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene In water; tert-butyl alcohol at 20℃; for 18h;40%
[3-(2-methyl-[1,3]dioxolan-2-yl)-propyl]-magnesium chloride
62026-31-7

[3-(2-methyl-[1,3]dioxolan-2-yl)-propyl]-magnesium chloride

C18H26O5
74712-32-6, 88293-64-5

C18H26O5

A

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1944-63-4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione

B

2,2-dimethyl-6-(2-methyl-[1,3]dioxolan-2-yl)-hexan-3-one
71594-11-1

2,2-dimethyl-6-(2-methyl-[1,3]dioxolan-2-yl)-hexan-3-one

C

(+)-3,3-ethylenedioxy-4,5-seco-19-norandrost-9-en-5,17-dione
24894-29-9

(+)-3,3-ethylenedioxy-4,5-seco-19-norandrost-9-en-5,17-dione

Conditions
ConditionsYield
In tetrahydrofuran at -70℃; for 1h; Yield given;
(1R,3aS,4S,7aS)-4-(2-Carboxy-ethyl)-1-hydroxy-7a-methyl-5-oxo-octahydro-indene-1-carboxylic acid
37134-59-1

(1R,3aS,4S,7aS)-4-(2-Carboxy-ethyl)-1-hydroxy-7a-methyl-5-oxo-octahydro-indene-1-carboxylic acid

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1944-63-4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione

Conditions
ConditionsYield
With sodium bismuthate In acetic acid
(S)-Halos-Parish ketone
17553-86-5

(S)-Halos-Parish ketone

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1944-63-4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: sodium tetrahydroborate / ethanol / 0 °C / Inert atmosphere
2.1: 1-methyl-1H-imidazole; iodine / tetrahydrofuran / 42 h / 20 °C / Inert atmosphere
3.1: dimethyl sulfoxide; sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C / Inert atmosphere
3.2: 18 h / 20 °C / Inert atmosphere
4.1: palladium on activated charcoal; hydrogen
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C
6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C
7.1: periodic acid / ethyl acetate / 20 °C
8.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C
View Scheme
Multi-step reaction with 8 steps
1.1: sodium tetrahydroborate / ethanol / 0 °C / Inert atmosphere
2.1: 1-methyl-1H-imidazole; iodine / tetrahydrofuran / 42 h / 20 °C / Inert atmosphere
3.1: dimethyl sulfoxide; sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C / Inert atmosphere
3.2: 18 h / 20 °C / Inert atmosphere
4.1: nickel(II) chloride hexahydrate; sodium tetrahydroborate / methanol / 1 h / -35 °C
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C
6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C
7.1: periodic acid / ethyl acetate / 20 °C
8.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C
View Scheme
Multi-step reaction with 8 steps
1.1: sodium tetrahydroborate / ethanol / 0 °C / Inert atmosphere
2.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
3.1: dimethyl sulfoxide; sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C / Inert atmosphere
3.2: 18 h / 20 °C / Inert atmosphere
4.1: palladium on activated charcoal; hydrogen
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C
6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C
7.1: periodic acid / ethyl acetate / 20 °C
8.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C
View Scheme
Multi-step reaction with 8 steps
1.1: sodium tetrahydroborate / ethanol / 0 °C / Inert atmosphere
2.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
3.1: dimethyl sulfoxide; sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C / Inert atmosphere
3.2: 18 h / 20 °C / Inert atmosphere
4.1: nickel(II) chloride hexahydrate; sodium tetrahydroborate / methanol / 1 h / -35 °C
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C
6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C
7.1: periodic acid / ethyl acetate / 20 °C
8.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C
View Scheme
C23H40O4Si

C23H40O4Si

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1944-63-4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: nickel(II) chloride hexahydrate; sodium tetrahydroborate / methanol / 1 h / -35 °C
2: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C
3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C
4: periodic acid / ethyl acetate / 20 °C
5: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1: palladium on activated charcoal; hydrogen
2: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C
3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C
4: periodic acid / ethyl acetate / 20 °C
5: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C
View Scheme
C23H42O4Si

C23H42O4Si

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1944-63-4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C
2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C
3: periodic acid / ethyl acetate / 20 °C
4: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C
View Scheme
C17H28O4

C17H28O4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1944-63-4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C
2: periodic acid / ethyl acetate / 20 °C
3: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C
View Scheme
(1S,7aS)-1-hydroxy-7a-methyl-2,3,7,7a-tetrahydro-1H-inden-5(6H)-one
16271-49-1

(1S,7aS)-1-hydroxy-7a-methyl-2,3,7,7a-tetrahydro-1H-inden-5(6H)-one

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1944-63-4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
2.1: dimethyl sulfoxide; sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C / Inert atmosphere
2.2: 18 h / 20 °C / Inert atmosphere
3.1: palladium on activated charcoal; hydrogen
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C
5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C
6.1: periodic acid / ethyl acetate / 20 °C
7.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C
View Scheme
Multi-step reaction with 7 steps
1.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
2.1: dimethyl sulfoxide; sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C / Inert atmosphere
2.2: 18 h / 20 °C / Inert atmosphere
3.1: nickel(II) chloride hexahydrate; sodium tetrahydroborate / methanol / 1 h / -35 °C
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C
5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C
6.1: periodic acid / ethyl acetate / 20 °C
7.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C
View Scheme
Multi-step reaction with 7 steps
1.1: 1-methyl-1H-imidazole; iodine / tetrahydrofuran / 42 h / 20 °C / Inert atmosphere
2.1: dimethyl sulfoxide; sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C / Inert atmosphere
2.2: 18 h / 20 °C / Inert atmosphere
3.1: palladium on activated charcoal; hydrogen
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C
5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C
6.1: periodic acid / ethyl acetate / 20 °C
7.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C
View Scheme
Multi-step reaction with 7 steps
1.1: 1-methyl-1H-imidazole; iodine / tetrahydrofuran / 42 h / 20 °C / Inert atmosphere
2.1: dimethyl sulfoxide; sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C / Inert atmosphere
2.2: 18 h / 20 °C / Inert atmosphere
3.1: nickel(II) chloride hexahydrate; sodium tetrahydroborate / methanol / 1 h / -35 °C
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C
5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C
6.1: periodic acid / ethyl acetate / 20 °C
7.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C
View Scheme
C17H26O4

C17H26O4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1944-63-4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: periodic acid / ethyl acetate / 20 °C
2: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C
View Scheme
(1S,7aS)-1-((tert-butyldimethylsilyl)oxy)-7a-methyl-1,2,3,6,7,7a-hexahydro-5H-inden-5-one
149789-99-1, 126541-53-5

(1S,7aS)-1-((tert-butyldimethylsilyl)oxy)-7a-methyl-1,2,3,6,7,7a-hexahydro-5H-inden-5-one

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1944-63-4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: dimethyl sulfoxide; sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C / Inert atmosphere
1.2: 18 h / 20 °C / Inert atmosphere
2.1: nickel(II) chloride hexahydrate; sodium tetrahydroborate / methanol / 1 h / -35 °C
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C
4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C
5.1: periodic acid / ethyl acetate / 20 °C
6.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C
View Scheme
Multi-step reaction with 6 steps
1.1: dimethyl sulfoxide; sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C / Inert atmosphere
1.2: 18 h / 20 °C / Inert atmosphere
2.1: palladium on activated charcoal; hydrogen
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C
4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C
5.1: periodic acid / ethyl acetate / 20 °C
6.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C
View Scheme
methanol
67-56-1

methanol

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1944-63-4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione

(3aS,7aS)-1,5-dioxo-4α-methylpropionic-3aα,4,5,6,7,7a-hexahydro-7a-methylindan
59005-87-7

(3aS,7aS)-1,5-dioxo-4α-methylpropionic-3aα,4,5,6,7,7a-hexahydro-7a-methylindan

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 23h;96%
With toluene-4-sulfonic acid for 2h; Esterification; Heating;90%
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1944-63-4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione

1,6,6a,7,8,9,9a,9b-octahydro-6a-methyl-<6aS-(6aα,9aβ,9bα)>cyclopenta<1>benzopyran-3(2H)-7-dione
39783-27-2

1,6,6a,7,8,9,9a,9b-octahydro-6a-methyl-<6aS-(6aα,9aβ,9bα)>cyclopenta<1>benzopyran-3(2H)-7-dione

Conditions
ConditionsYield
With sodium acetate; acetic anhydride for 4h; Heating;93%
With perchloric acid; acetic anhydride In ethyl acetate81%
With perchloric acid; acetic anhydride In ethyl acetate80%
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1944-63-4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione

A

(3aS,9aS,9bS)-3a-Methyl-1,2,4,6,8,9,9a,9b-octahydro-3aH-6-aza-cyclopenta[a]naphthalene-3,7-dione
24967-14-4

(3aS,9aS,9bS)-3a-Methyl-1,2,4,6,8,9,9a,9b-octahydro-3aH-6-aza-cyclopenta[a]naphthalene-3,7-dione

B

(3aS,9bS)-3a-Methyl-1,2,4,5,6,8,9,9b-octahydro-3aH-6-aza-cyclopenta[a]naphthalene-3,7-dione

(3aS,9bS)-3a-Methyl-1,2,4,5,6,8,9,9b-octahydro-3aH-6-aza-cyclopenta[a]naphthalene-3,7-dione

Conditions
ConditionsYield
With formic acid; ammonium bicarbonate at 120℃; for 1h; Yields of byproduct given;A 59%
B n/a
With formic acid; ammonium bicarbonate at 120℃; for 1h; Yield given. Yields of byproduct given;
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1944-63-4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione

(3aS,7aS)-4-ethylidene-5,6,7,7a-tetrahydro-7a-methylindan-1,5-dione

(3aS,7aS)-4-ethylidene-5,6,7,7a-tetrahydro-7a-methylindan-1,5-dione

Conditions
ConditionsYield
With pyridine; copper diacetate; [bis(acetoxy)iodo]benzene In benzene for 8h; Decarboxylation; Heating;40%
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1944-63-4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione

pivaloyl chloride
3282-30-2

pivaloyl chloride

C18H26O5
74712-32-6, 88293-64-5

C18H26O5

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at -20℃; Yield given;
With triethylamine In tetrahydrofuran at -30℃; for 3.5h; Temperature; Inert atmosphere;
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1944-63-4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione

17β-Hydroxy-5-oxo-des-A-10-aza-oestran
17261-92-6

17β-Hydroxy-5-oxo-des-A-10-aza-oestran

Conditions
ConditionsYield
With hydrogenchloride; formic acid; sodium cyanoborohydride; ammonium bicarbonate 1.) 120 deg C, 1 h, 2.) MeOH, pH 1.5-2, room temperature, 48 h; Yield given. Multistep reaction;
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1944-63-4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione

estradiol
50-28-2

estradiol

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: 90 percent / p-TsOH / 2 h / Heating
2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3.1: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating
4.1: 85 percent / K2CO3 / methanol / 20 °C
5.1: 78 percent / 4-DMAP / 3 h / 20 °C
6.1: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C
7.1: KBH4 / methanol / 1 h / 0 °C
8.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C
9.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation
10.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C
10.2: NCS / tetrahydrofuran / -105 - 25 °C
10.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C
11.1: KNH(CH2)3NH2 / tetrahydrofuran / 15 h / 20 °C
11.2: 48 percent HF / acetonitrile / 20 °C
11.3: 45 percent / TFA; Et3SiH / benzene / 15 h / 20 °C
12.1: 80 percent / TFA; Pb(OTFA)4 / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 12 steps
1.1: 90 percent / p-TsOH / 2 h / Heating
2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3.1: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating
4.1: 85 percent / K2CO3 / methanol / 20 °C
5.1: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C
6.1: t-BuOK / tetrahydrofuran / 0 °C
7.1: KBH4 / methanol / 1 h / 0 °C
8.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C
9.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation
10.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C
10.2: NCS / tetrahydrofuran / -105 - 25 °C
10.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C
11.1: KNH(CH2)3NH2 / tetrahydrofuran / 15 h / 20 °C
11.2: 48 percent HF / acetonitrile / 20 °C
11.3: 45 percent / TFA; Et3SiH / benzene / 15 h / 20 °C
12.1: 80 percent / TFA; Pb(OTFA)4 / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 13 steps
1.1: 90 percent / p-TsOH / 2 h / Heating
2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3.1: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis
4.1: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating
5.1: 85 percent / K2CO3 / methanol / 20 °C
6.1: 78 percent / 4-DMAP / 3 h / 20 °C
7.1: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C
8.1: KBH4 / methanol / 1 h / 0 °C
9.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C
10.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation
11.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C
11.2: NCS / tetrahydrofuran / -105 - 25 °C
11.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C
12.1: KNH(CH2)3NH2 / tetrahydrofuran / 15 h / 20 °C
12.2: 48 percent HF / acetonitrile / 20 °C
12.3: 45 percent / TFA; Et3SiH / benzene / 15 h / 20 °C
13.1: 80 percent / TFA; Pb(OTFA)4 / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 13 steps
1.1: 90 percent / p-TsOH / 2 h / Heating
2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3.1: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis
4.1: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating
5.1: 85 percent / K2CO3 / methanol / 20 °C
6.1: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C
7.1: t-BuOK / tetrahydrofuran / 0 °C
8.1: KBH4 / methanol / 1 h / 0 °C
9.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C
10.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation
11.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C
11.2: NCS / tetrahydrofuran / -105 - 25 °C
11.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C
12.1: KNH(CH2)3NH2 / tetrahydrofuran / 15 h / 20 °C
12.2: 48 percent HF / acetonitrile / 20 °C
12.3: 45 percent / TFA; Et3SiH / benzene / 15 h / 20 °C
13.1: 80 percent / TFA; Pb(OTFA)4 / 0.5 h / 20 °C
View Scheme
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1944-63-4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione

(3aS,4R,7aS)-7a-Methyl-4-vinyl-2,3,3a,4,7,7a-hexahydro-inden-1-one

(3aS,4R,7aS)-7a-Methyl-4-vinyl-2,3,3a,4,7,7a-hexahydro-inden-1-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 90 percent / p-TsOH / 2 h / Heating
2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating
4: 85 percent / K2CO3 / methanol / 20 °C
5: 78 percent / 4-DMAP / 3 h / 20 °C
6: 65 percent / t-BuOK / tetrahydrofuran / 0 °C
View Scheme
Multi-step reaction with 6 steps
1: 90 percent / p-TsOH / 2 h / Heating
2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating
4: 85 percent / K2CO3 / methanol / 20 °C
5: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C
6: t-BuOK / tetrahydrofuran / 0 °C
View Scheme
Multi-step reaction with 7 steps
1: 90 percent / p-TsOH / 2 h / Heating
2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis
4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating
5: 85 percent / K2CO3 / methanol / 20 °C
6: 78 percent / 4-DMAP / 3 h / 20 °C
7: 65 percent / t-BuOK / tetrahydrofuran / 0 °C
View Scheme
Multi-step reaction with 7 steps
1: 90 percent / p-TsOH / 2 h / Heating
2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis
4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating
5: 85 percent / K2CO3 / methanol / 20 °C
6: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C
7: t-BuOK / tetrahydrofuran / 0 °C
View Scheme
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1944-63-4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione

(3aS,7aS)-7a-Methyl-4-vinyl-2,3,3a,6,7,7a-hexahydro-inden-1-one
250331-22-7

(3aS,7aS)-7a-Methyl-4-vinyl-2,3,3a,6,7,7a-hexahydro-inden-1-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 90 percent / p-TsOH / 2 h / Heating
2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating
4: 85 percent / K2CO3 / methanol / 20 °C
5: 78 percent / 4-DMAP / 3 h / 20 °C
6: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C
View Scheme
Multi-step reaction with 6 steps
1: 90 percent / p-TsOH / 2 h / Heating
2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating
4: 85 percent / K2CO3 / methanol / 20 °C
5: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C
6: t-BuOK / tetrahydrofuran / 0 °C
View Scheme
Multi-step reaction with 7 steps
1: 90 percent / p-TsOH / 2 h / Heating
2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis
4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating
5: 85 percent / K2CO3 / methanol / 20 °C
6: 78 percent / 4-DMAP / 3 h / 20 °C
7: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C
View Scheme
Multi-step reaction with 7 steps
1: 90 percent / p-TsOH / 2 h / Heating
2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis
4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating
5: 85 percent / K2CO3 / methanol / 20 °C
6: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C
7: t-BuOK / tetrahydrofuran / 0 °C
View Scheme
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1944-63-4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione

(1S,3aS,7aS)-7a-Methyl-4-vinyl-2,3,3a,6,7,7a-hexahydro-1H-inden-1-ol
332900-29-5

(1S,3aS,7aS)-7a-Methyl-4-vinyl-2,3,3a,6,7,7a-hexahydro-1H-inden-1-ol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 90 percent / p-TsOH / 2 h / Heating
2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating
4: 85 percent / K2CO3 / methanol / 20 °C
5: 78 percent / 4-DMAP / 3 h / 20 °C
6: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C
7: KBH4 / methanol / 1 h / 0 °C
View Scheme
Multi-step reaction with 7 steps
1: 90 percent / p-TsOH / 2 h / Heating
2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating
4: 85 percent / K2CO3 / methanol / 20 °C
5: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C
6: t-BuOK / tetrahydrofuran / 0 °C
7: KBH4 / methanol / 1 h / 0 °C
View Scheme
Multi-step reaction with 8 steps
1: 90 percent / p-TsOH / 2 h / Heating
2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis
4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating
5: 85 percent / K2CO3 / methanol / 20 °C
6: 78 percent / 4-DMAP / 3 h / 20 °C
7: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C
8: KBH4 / methanol / 1 h / 0 °C
View Scheme
Multi-step reaction with 8 steps
1: 90 percent / p-TsOH / 2 h / Heating
2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis
4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating
5: 85 percent / K2CO3 / methanol / 20 °C
6: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C
7: t-BuOK / tetrahydrofuran / 0 °C
8: KBH4 / methanol / 1 h / 0 °C
View Scheme
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1944-63-4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione

(3aS,7aS)-4α-ethenyl-5α-hydroxy-1-oxo-,4,5,6,7,7a-hexahydro-7a-methylindan
250331-20-5

(3aS,7aS)-4α-ethenyl-5α-hydroxy-1-oxo-,4,5,6,7,7a-hexahydro-7a-methylindan

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 90 percent / p-TsOH / 2 h / Heating
2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating
4: 85 percent / K2CO3 / methanol / 20 °C
View Scheme
Multi-step reaction with 5 steps
1: 90 percent / p-TsOH / 2 h / Heating
2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis
4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating
5: 85 percent / K2CO3 / methanol / 20 °C
View Scheme
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1944-63-4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione

(3aS,7aS)-4α-ethenyl-5α-formyloxy-1-oxo-,4,5,6,7,7a-hexahydro-7a-methylindan
250331-19-2

(3aS,7aS)-4α-ethenyl-5α-formyloxy-1-oxo-,4,5,6,7,7a-hexahydro-7a-methylindan

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 90 percent / p-TsOH / 2 h / Heating
2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating
View Scheme
Multi-step reaction with 4 steps
1: 90 percent / p-TsOH / 2 h / Heating
2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis
4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating
View Scheme
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1944-63-4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione

(3aS,5aR,9bS)-7-Hydroxy-3a-methyl-decahydro-6-oxa-cyclopenta[a]naphthalen-3-one

(3aS,5aR,9bS)-7-Hydroxy-3a-methyl-decahydro-6-oxa-cyclopenta[a]naphthalen-3-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 90 percent / p-TsOH / 2 h / Heating
2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
View Scheme
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1944-63-4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione

(3aS,7aS)-1,5-dihydroxy-4α-β-propionolactone-3a,4,5,6,7,7a-hexahydro-7a-methylindan

(3aS,7aS)-1,5-dihydroxy-4α-β-propionolactone-3a,4,5,6,7,7a-hexahydro-7a-methylindan

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 90 percent / p-TsOH / 2 h / Heating
2: 85 percent / KBH4 / methanol / 0.5 h / 0 °C
View Scheme
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1944-63-4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione

(3aS,7aS)-4α-ethenyl-5α-methanesulfonyl-1-oxo-,4,5,6,7,7a-hexahydro-7a-methylindan
250331-21-6

(3aS,7aS)-4α-ethenyl-5α-methanesulfonyl-1-oxo-,4,5,6,7,7a-hexahydro-7a-methylindan

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 90 percent / p-TsOH / 2 h / Heating
2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating
4: 85 percent / K2CO3 / methanol / 20 °C
5: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C
View Scheme
Multi-step reaction with 6 steps
1: 90 percent / p-TsOH / 2 h / Heating
2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis
4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating
5: 85 percent / K2CO3 / methanol / 20 °C
6: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C
View Scheme
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1944-63-4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione

(3aS,7aS)-5-formyloxy-4α-(2'-iodoethyl)-1-oxo-3a,4,5,6,7,7a-hexahydro-7a-methylindan
250331-18-1

(3aS,7aS)-5-formyloxy-4α-(2'-iodoethyl)-1-oxo-3a,4,5,6,7,7a-hexahydro-7a-methylindan

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 90 percent / p-TsOH / 2 h / Heating
2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis
View Scheme
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1944-63-4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione

A

(3aS,7aS)-4α-ethenyl-1-[(tert-butyldimethylsilyl)oxy]-3a-methyl-3a,6,7,7a-tetrahydro-4-indene
250331-25-0

(3aS,7aS)-4α-ethenyl-1-[(tert-butyldimethylsilyl)oxy]-3a-methyl-3a,6,7,7a-tetrahydro-4-indene

B

(η6-4-trimethylsilylthiepin-1,1-dioxide)chromium(0)

(η6-4-trimethylsilylthiepin-1,1-dioxide)chromium(0)

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 90 percent / p-TsOH / 2 h / Heating
2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating
4: 85 percent / K2CO3 / methanol / 20 °C
5: 78 percent / 4-DMAP / 3 h / 20 °C
6: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C
7: KBH4 / methanol / 1 h / 0 °C
8: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C
View Scheme
Multi-step reaction with 8 steps
1: 90 percent / p-TsOH / 2 h / Heating
2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating
4: 85 percent / K2CO3 / methanol / 20 °C
5: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C
6: t-BuOK / tetrahydrofuran / 0 °C
7: KBH4 / methanol / 1 h / 0 °C
8: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C
View Scheme
Multi-step reaction with 9 steps
1: 90 percent / p-TsOH / 2 h / Heating
2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis
4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating
5: 85 percent / K2CO3 / methanol / 20 °C
6: 78 percent / 4-DMAP / 3 h / 20 °C
7: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C
8: KBH4 / methanol / 1 h / 0 °C
9: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C
View Scheme
Multi-step reaction with 9 steps
1: 90 percent / p-TsOH / 2 h / Heating
2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis
4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating
5: 85 percent / K2CO3 / methanol / 20 °C
6: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C
7: t-BuOK / tetrahydrofuran / 0 °C
8: KBH4 / methanol / 1 h / 0 °C
9: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C
View Scheme
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1944-63-4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione

(3aS,7aS)-5-hydroxy-4α-β-propionolactone-1-[(tert-butyldimethylsilyl)oxy]-3a,4,5,6,7,7a-hexahydro-7a-methylindan

(3aS,7aS)-5-hydroxy-4α-β-propionolactone-1-[(tert-butyldimethylsilyl)oxy]-3a,4,5,6,7,7a-hexahydro-7a-methylindan

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 90 percent / p-TsOH / 2 h / Heating
2: 85 percent / KBH4 / methanol / 0.5 h / 0 °C
3: 85 percent / imidazole / dimethylformamide / 18 h / 20 °C
View Scheme
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1944-63-4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione

3-(tert-butyl-dimethyl-silanyloxy)-3a-methyl-dodecahydro-6-oxa-cyclopenta[a]naphthalen-7-ol

3-(tert-butyl-dimethyl-silanyloxy)-3a-methyl-dodecahydro-6-oxa-cyclopenta[a]naphthalen-7-ol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 90 percent / p-TsOH / 2 h / Heating
2: 85 percent / KBH4 / methanol / 0.5 h / 0 °C
3: 85 percent / imidazole / dimethylformamide / 18 h / 20 °C
4: DIBALH / CH2Cl2; hexane / 1 h / -78 °C
View Scheme
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1944-63-4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione

(3aS,7aS)-4α-ethenyl-1-oxo-5-(4'-methylbenzenesulfonyl)-3a,4,5,6,7,7a-hexahydro-7a-methylindan
250331-24-9

(3aS,7aS)-4α-ethenyl-1-oxo-5-(4'-methylbenzenesulfonyl)-3a,4,5,6,7,7a-hexahydro-7a-methylindan

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 90 percent / p-TsOH / 2 h / Heating
2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating
4: 85 percent / K2CO3 / methanol / 20 °C
5: 78 percent / 4-DMAP / 3 h / 20 °C
View Scheme
Multi-step reaction with 6 steps
1: 90 percent / p-TsOH / 2 h / Heating
2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis
4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating
5: 85 percent / K2CO3 / methanol / 20 °C
6: 78 percent / 4-DMAP / 3 h / 20 °C
View Scheme
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1944-63-4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione

(3aS,7aS)-5-formyloxy-4α-(2'-iodoethylene)-1-[tert-(butyldimethyl)silyloxy]-3a,4,5,6,7,7a-hexahydro-7a-methylindan

(3aS,7aS)-5-formyloxy-4α-(2'-iodoethylene)-1-[tert-(butyldimethyl)silyloxy]-3a,4,5,6,7,7a-hexahydro-7a-methylindan

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 90 percent / p-TsOH / 2 h / Heating
2: 85 percent / KBH4 / methanol / 0.5 h / 0 °C
3: 85 percent / imidazole / dimethylformamide / 18 h / 20 °C
4: DIBALH / CH2Cl2; hexane / 1 h / -78 °C
5: 75 percent / I2; iodobenzene diacetate / cyclohexane / Photolysis
View Scheme
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1944-63-4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione

1β-hydroxy-3-trimethylsilylestra-1,3,5(10)-triene
250331-30-7

1β-hydroxy-3-trimethylsilylestra-1,3,5(10)-triene

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: 90 percent / p-TsOH / 2 h / Heating
2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3.1: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating
4.1: 85 percent / K2CO3 / methanol / 20 °C
5.1: 78 percent / 4-DMAP / 3 h / 20 °C
6.1: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C
7.1: KBH4 / methanol / 1 h / 0 °C
8.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C
9.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation
10.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C
10.2: NCS / tetrahydrofuran / -105 - 25 °C
10.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C
11.1: KNH(CH2)3NH2 / tetrahydrofuran / 15 h / 20 °C
11.2: 48 percent HF / acetonitrile / 20 °C
11.3: 45 percent / TFA; Et3SiH / benzene / 15 h / 20 °C
View Scheme
Multi-step reaction with 11 steps
1.1: 90 percent / p-TsOH / 2 h / Heating
2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3.1: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating
4.1: 85 percent / K2CO3 / methanol / 20 °C
5.1: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C
6.1: t-BuOK / tetrahydrofuran / 0 °C
7.1: KBH4 / methanol / 1 h / 0 °C
8.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C
9.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation
10.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C
10.2: NCS / tetrahydrofuran / -105 - 25 °C
10.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C
11.1: KNH(CH2)3NH2 / tetrahydrofuran / 15 h / 20 °C
11.2: 48 percent HF / acetonitrile / 20 °C
11.3: 45 percent / TFA; Et3SiH / benzene / 15 h / 20 °C
View Scheme
Multi-step reaction with 12 steps
1.1: 90 percent / p-TsOH / 2 h / Heating
2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3.1: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis
4.1: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating
5.1: 85 percent / K2CO3 / methanol / 20 °C
6.1: 78 percent / 4-DMAP / 3 h / 20 °C
7.1: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C
8.1: KBH4 / methanol / 1 h / 0 °C
9.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C
10.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation
11.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C
11.2: NCS / tetrahydrofuran / -105 - 25 °C
11.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C
12.1: KNH(CH2)3NH2 / tetrahydrofuran / 15 h / 20 °C
12.2: 48 percent HF / acetonitrile / 20 °C
12.3: 45 percent / TFA; Et3SiH / benzene / 15 h / 20 °C
View Scheme
Multi-step reaction with 12 steps
1.1: 90 percent / p-TsOH / 2 h / Heating
2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3.1: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis
4.1: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating
5.1: 85 percent / K2CO3 / methanol / 20 °C
6.1: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C
7.1: t-BuOK / tetrahydrofuran / 0 °C
8.1: KBH4 / methanol / 1 h / 0 °C
9.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C
10.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation
11.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C
11.2: NCS / tetrahydrofuran / -105 - 25 °C
11.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C
12.1: KNH(CH2)3NH2 / tetrahydrofuran / 15 h / 20 °C
12.2: 48 percent HF / acetonitrile / 20 °C
12.3: 45 percent / TFA; Et3SiH / benzene / 15 h / 20 °C
View Scheme
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1944-63-4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione

17-(tert-butyl-dimethyl-silanyloxy)-13-methyl-3-trimethylsilanyl-7,8,12,13,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthrene

17-(tert-butyl-dimethyl-silanyloxy)-13-methyl-3-trimethylsilanyl-7,8,12,13,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthrene

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: 90 percent / p-TsOH / 2 h / Heating
2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3.1: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating
4.1: 85 percent / K2CO3 / methanol / 20 °C
5.1: 78 percent / 4-DMAP / 3 h / 20 °C
6.1: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C
7.1: KBH4 / methanol / 1 h / 0 °C
8.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C
9.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation
10.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C
10.2: NCS / tetrahydrofuran / -105 - 25 °C
10.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C
11.1: potassium 3-aminopropylamide / tetrahydrofuran / 15 h / 20 °C
View Scheme
Multi-step reaction with 11 steps
1.1: 90 percent / p-TsOH / 2 h / Heating
2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3.1: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating
4.1: 85 percent / K2CO3 / methanol / 20 °C
5.1: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C
6.1: t-BuOK / tetrahydrofuran / 0 °C
7.1: KBH4 / methanol / 1 h / 0 °C
8.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C
9.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation
10.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C
10.2: NCS / tetrahydrofuran / -105 - 25 °C
10.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C
11.1: potassium 3-aminopropylamide / tetrahydrofuran / 15 h / 20 °C
View Scheme
Multi-step reaction with 12 steps
1.1: 90 percent / p-TsOH / 2 h / Heating
2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3.1: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis
4.1: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating
5.1: 85 percent / K2CO3 / methanol / 20 °C
6.1: 78 percent / 4-DMAP / 3 h / 20 °C
7.1: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C
8.1: KBH4 / methanol / 1 h / 0 °C
9.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C
10.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation
11.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C
11.2: NCS / tetrahydrofuran / -105 - 25 °C
11.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C
12.1: potassium 3-aminopropylamide / tetrahydrofuran / 15 h / 20 °C
View Scheme
Multi-step reaction with 12 steps
1.1: 90 percent / p-TsOH / 2 h / Heating
2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3.1: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis
4.1: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating
5.1: 85 percent / K2CO3 / methanol / 20 °C
6.1: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C
7.1: t-BuOK / tetrahydrofuran / 0 °C
8.1: KBH4 / methanol / 1 h / 0 °C
9.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C
10.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation
11.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C
11.2: NCS / tetrahydrofuran / -105 - 25 °C
11.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C
12.1: potassium 3-aminopropylamide / tetrahydrofuran / 15 h / 20 °C
View Scheme
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1944-63-4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione

1-[(tert-butyldimethylsilyl)oxy]-3-trimethylsilyl-9Hβ-estra-1,3,5(10),7-tetraene
250331-27-2

1-[(tert-butyldimethylsilyl)oxy]-3-trimethylsilyl-9Hβ-estra-1,3,5(10),7-tetraene

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: 90 percent / p-TsOH / 2 h / Heating
2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3.1: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating
4.1: 85 percent / K2CO3 / methanol / 20 °C
5.1: 78 percent / 4-DMAP / 3 h / 20 °C
6.1: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C
7.1: KBH4 / methanol / 1 h / 0 °C
8.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C
9.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation
10.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C
10.2: NCS / tetrahydrofuran / -105 - 25 °C
10.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C
View Scheme
Multi-step reaction with 10 steps
1.1: 90 percent / p-TsOH / 2 h / Heating
2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3.1: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating
4.1: 85 percent / K2CO3 / methanol / 20 °C
5.1: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C
6.1: t-BuOK / tetrahydrofuran / 0 °C
7.1: KBH4 / methanol / 1 h / 0 °C
8.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C
9.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation
10.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C
10.2: NCS / tetrahydrofuran / -105 - 25 °C
10.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C
View Scheme
Multi-step reaction with 11 steps
1.1: 90 percent / p-TsOH / 2 h / Heating
2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3.1: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis
4.1: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating
5.1: 85 percent / K2CO3 / methanol / 20 °C
6.1: 78 percent / 4-DMAP / 3 h / 20 °C
7.1: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C
8.1: KBH4 / methanol / 1 h / 0 °C
9.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C
10.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation
11.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C
11.2: NCS / tetrahydrofuran / -105 - 25 °C
11.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C
View Scheme
Multi-step reaction with 11 steps
1.1: 90 percent / p-TsOH / 2 h / Heating
2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3.1: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis
4.1: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating
5.1: 85 percent / K2CO3 / methanol / 20 °C
6.1: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C
7.1: t-BuOK / tetrahydrofuran / 0 °C
8.1: KBH4 / methanol / 1 h / 0 °C
9.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C
10.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation
11.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C
11.2: NCS / tetrahydrofuran / -105 - 25 °C
11.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C
View Scheme
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1944-63-4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione

17-(tert-butyl-dimethyl-silanyloxy)-13-methyl-3-trimethylsilanyl-7,11,12,13,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthrene

17-(tert-butyl-dimethyl-silanyloxy)-13-methyl-3-trimethylsilanyl-7,11,12,13,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthrene

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: 90 percent / p-TsOH / 2 h / Heating
2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3.1: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating
4.1: 85 percent / K2CO3 / methanol / 20 °C
5.1: 78 percent / 4-DMAP / 3 h / 20 °C
6.1: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C
7.1: KBH4 / methanol / 1 h / 0 °C
8.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C
9.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation
10.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C
10.2: NCS / tetrahydrofuran / -105 - 25 °C
10.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C
11.1: potassium 3-aminopropylamide / tetrahydrofuran / 15 h / 20 °C
View Scheme
Multi-step reaction with 11 steps
1.1: 90 percent / p-TsOH / 2 h / Heating
2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3.1: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating
4.1: 85 percent / K2CO3 / methanol / 20 °C
5.1: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C
6.1: t-BuOK / tetrahydrofuran / 0 °C
7.1: KBH4 / methanol / 1 h / 0 °C
8.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C
9.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation
10.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C
10.2: NCS / tetrahydrofuran / -105 - 25 °C
10.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C
11.1: potassium 3-aminopropylamide / tetrahydrofuran / 15 h / 20 °C
View Scheme
Multi-step reaction with 12 steps
1.1: 90 percent / p-TsOH / 2 h / Heating
2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3.1: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis
4.1: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating
5.1: 85 percent / K2CO3 / methanol / 20 °C
6.1: 78 percent / 4-DMAP / 3 h / 20 °C
7.1: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C
8.1: KBH4 / methanol / 1 h / 0 °C
9.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C
10.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation
11.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C
11.2: NCS / tetrahydrofuran / -105 - 25 °C
11.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C
12.1: potassium 3-aminopropylamide / tetrahydrofuran / 15 h / 20 °C
View Scheme
Multi-step reaction with 12 steps
1.1: 90 percent / p-TsOH / 2 h / Heating
2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3.1: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis
4.1: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating
5.1: 85 percent / K2CO3 / methanol / 20 °C
6.1: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C
7.1: t-BuOK / tetrahydrofuran / 0 °C
8.1: KBH4 / methanol / 1 h / 0 °C
9.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C
10.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation
11.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C
11.2: NCS / tetrahydrofuran / -105 - 25 °C
11.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C
12.1: potassium 3-aminopropylamide / tetrahydrofuran / 15 h / 20 °C
View Scheme
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1944-63-4

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione

(1S,2S,5S,9S,13S)-6-[(tert-butyldimethylsilyl)oxy]-5-methyl-15-trimethylsilyl-18-thiatetracyclo[11.4.1.02,10.05,9]-10,14,16-triene-18,18-dioxide
250331-26-1

(1S,2S,5S,9S,13S)-6-[(tert-butyldimethylsilyl)oxy]-5-methyl-15-trimethylsilyl-18-thiatetracyclo[11.4.1.02,10.05,9]-10,14,16-triene-18,18-dioxide

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 90 percent / p-TsOH / 2 h / Heating
2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating
4: 85 percent / K2CO3 / methanol / 20 °C
5: 78 percent / 4-DMAP / 3 h / 20 °C
6: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C
7: KBH4 / methanol / 1 h / 0 °C
8: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C
9: 70 percent / 1,2-dichloro-ethane / UV-irradiation
View Scheme
Multi-step reaction with 9 steps
1: 90 percent / p-TsOH / 2 h / Heating
2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating
4: 85 percent / K2CO3 / methanol / 20 °C
5: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C
6: t-BuOK / tetrahydrofuran / 0 °C
7: KBH4 / methanol / 1 h / 0 °C
8: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C
9: 70 percent / 1,2-dichloro-ethane / UV-irradiation
View Scheme
Multi-step reaction with 10 steps
1: 90 percent / p-TsOH / 2 h / Heating
2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis
4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating
5: 85 percent / K2CO3 / methanol / 20 °C
6: 78 percent / 4-DMAP / 3 h / 20 °C
7: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C
8: KBH4 / methanol / 1 h / 0 °C
9: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C
10: 70 percent / 1,2-dichloro-ethane / UV-irradiation
View Scheme
Multi-step reaction with 10 steps
1: 90 percent / p-TsOH / 2 h / Heating
2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis
4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating
5: 85 percent / K2CO3 / methanol / 20 °C
6: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C
7: t-BuOK / tetrahydrofuran / 0 °C
8: KBH4 / methanol / 1 h / 0 °C
9: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C
10: 70 percent / 1,2-dichloro-ethane / UV-irradiation
View Scheme

1944-63-4Relevant articles and documents

Synthesis of DOHNAA, a Mycobacterium tuberculosis Cholesterol CD Ring Catabolite and FadD3 Substrate

Stubbing, Louise A.,Lott, J. Shaun,Dawes, Stephanie S.,Furkert, Daniel P.,Brimble, Margaret A.

, p. 6075 - 6083 (2015)

DOHNAA (2) is a key catabolite in the Mycobacterium tuberculosis (Mtb) cholesterol degradation pathway. The CoA ester of 2 has been implicated in regulation of gene transcription that is ultimately responsible for degradation of the C and D rings of cholesterol. A synthetic route to 2 is reported here, by a key DMSO-mediated Morita-Bayliss-Hillman-type alkylation of the Hajos-Parrish dione. As DOHNAA has to date only been available from microbial sources in very small quantities, the synthesis described will enable further studies of the enzymes involved in cholesterol degradation in Mtb and facilitate ongoing structure-activity studies based on this compound scaffold.

Microbiological degradation of bile acids. Nitrogenous hexahydroindane derivatives formed from cholic acid by Streptomyces rubescens

Hayakawa,Hashimoto,Onaka

, p. 745 - 755 (2007/10/06)

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