126784-20-1

Basic information

• Product Name: (4aR,6aS,9aS,9bS)-6a-methyloctahydrocyclopenta[f]chromene-3,7(2H,8H)-dione
• Synonyms: Cyclopenta[f][1]benzopyran-3,7-dione,decahydro-6a-methyl-,[4aR-(4aα,6aα,9aβ,9bα)]-; Sitolactone; Cyclopenta[f][1]benzopyran-3,7-dione,decahydro-6a-methyl-,(4aR,6aS,9aS,9bS)-; 3aα-H-4α-[3'-propionic acid]-5α-hydroxy-7aβ-methyl-hexahydro-1-indanone-δ-lactone
• CAS NO: 126784-20-1
• Molecular Formula: C₁₃H₁₈O₃
• Molecular Weight: 222.28000
• Mol File: 126784-20-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (4aR,6aS,9aS,9bS)-6a-methyloctahydrocyclopenta[f]chromene-3,7(2H,8H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (4aR,6aS,9aS,9bS)-6a-methyloctahydrocyclopenta[f]chromene-3,7(2H,8H)-dione(126784-20-1)
• EPA Substance Registry System: (4aR,6aS,9aS,9bS)-6a-methyloctahydrocyclopenta[f]chromene-3,7(2H,8H)-dione(126784-20-1)

Safety Data

• Hazardous Substances Data: 126784-20-1(Hazardous Substances Data)

Usage

General Description

(4aR,6aS,9aS,9bS)-6a-methyloctahydrocyclopenta[f]chromene-3,7(2H,8H)-dione is a chemical compound with a complex and specific molecular structure. It is a dione, meaning it contains two carbonyl groups, and is also a cyclopentane derivative. The presence of a methyl group at the 6a position adds to its chemical properties and reactivity. (4aR,6aS,9aS,9bS)-6a-methyloctahydrocyclopenta[f]chromene-3,7(2H,8H)-dione may have potential uses in medicinal chemistry, as it is a cyclopentane-fused lactone, which can be found in natural products with biological activity. Further research and analysis of this chemical are needed to fully understand its potential applications and properties.

Synthetic route

Lithocholic acid (434-13-9) → 3aα-H-4α-<3'-propionic acid>-5α-hydroxy-7aβ-methyl-hexahydro-1-indanone-δ-lactone (126784-20-1)

Conditions	Yield
In water at 30℃; for 48h; mutant strain of Nocardia corallina NG-511;	39%

lithocholic acid → 3aα-H-4α-<3'-propionic acid>-5α-hydroxy-7aβ-methyl-hexahydro-1-indanone-δ-lactone (126784-20-1)

Conditions	Yield
at 30℃; for 48h; Nocardia corallina IFO 3338 strain NG-511;	39%

cholesterol (57-88-5) → 3aα-H-4α-<3'-propionic acid>-5α-hydroxy-7aβ-methyl-hexahydro-1-indanone-δ-lactone (126784-20-1)

Conditions	Yield
In water at 30℃; for 48h; mutant strain of Nocardia corallina NG-511;	35%
at 30℃; for 48h; Nocardia corallina IFO 3338 strain NG-511;	35%

progesterone (57-83-0) → 3aα-H-4α-<3'-propionic acid>-5α-hydroxy-7aβ-methyl-hexahydro-1-indanone-δ-lactone (126784-20-1)

Conditions	Yield
In water at 30℃; for 48h; mutant strain of Nocardia corallina NG-511;	30%

Progesterone (57-83-0) → 3aα-H-4α-<3'-propionic acid>-5α-hydroxy-7aβ-methyl-hexahydro-1-indanone-δ-lactone (126784-20-1)

Conditions	Yield
at 30℃; for 48h; Nocardia corallina IFO 3338 strain NG-511;	30%

β-sitosterol (83-46-5) → 3aα-H-4α-<3'-propionic acid>-5α-hydroxy-7aβ-methyl-hexahydro-1-indanone-δ-lactone (126784-20-1)

Conditions	Yield
In water at 30℃; for 48h; mutant strain of Nocardia corallina NG-511;	16%

β-sitosterol (257939-67-6) → 3aα-H-4α-<3'-propionic acid>-5α-hydroxy-7aβ-methyl-hexahydro-1-indanone-δ-lactone (126784-20-1)

Conditions	Yield
at 30℃; for 48h; Nocardia corallina IFO 3338 strain NG-511;	16%

Cholest-4-en-3-one (601-57-0) → 3aα-H-4α-<3'-propionic acid>-5α-hydroxy-7aβ-methyl-hexahydro-1-indanone-δ-lactone (126784-20-1)

Conditions	Yield
In water at 30℃; for 48h; mutant strain of Nocardia corallina NG-511;	15%
at 30℃; for 48h; Nocardia corallina IFO 3338 strain NG-511;	15%

Cholestanol (80-97-7) → 3aα-H-4α-<3'-propionic acid>-5α-hydroxy-7aβ-methyl-hexahydro-1-indanone-δ-lactone (126784-20-1)

Conditions	Yield
In water at 30℃; for 48h; mutant strain of Nocardia corallina NG-511;	9%
at 30℃; for 48h; Nocardia corallina IFO 3338 strain NG-511;	9%

cholic acid (81-25-4) → 3aα-H-4α-<3'-propionic acid>-5α-hydroxy-7aβ-methyl-hexahydro-1-indanone-δ-lactone (126784-20-1)

Conditions	Yield
In water at 30℃; for 48h; mutant strain of Nocardia corallina NG-511;	6%

cholic acid → 3aα-H-4α-<3'-propionic acid>-5α-hydroxy-7aβ-methyl-hexahydro-1-indanone-δ-lactone (126784-20-1)

Conditions	Yield
at 30℃; for 48h; Nocardia corallina IFO 3338 strain NG-511;	6%

Deoxycholic acid (83-44-3) → 12β-hydroxy-1,4-androstadiene-3,17-dione (28840-96-2) + 3aα-H-4α-<3'-propionic acid>-5α-hydroxy-7aβ-methyl-hexahydro-1-indanone-δ-lactone (126784-20-1) + 3,12β-dihydroxy-9,10-seco-1,3,5(10)-androstatriene-9,17-dione (79683-94-6) + 12α-hydroxyandrosta-1,4-dien-3,17-dione (59531-53-2)

Conditions	Yield
at 30℃; microbial degradation by Pseudomonas sp. MR108; Yield given. Yields of byproduct given;
at 30℃; microbial degradation by Pseudumonas sp. MR108; Yield given. Yields of byproduct given;

cholesterol (57-88-5) → 3aα-H-4α-<3'-propionic acid>-5α-hydroxy-7aβ-methyl-hexahydro-1-indanone-δ-lactone (126784-20-1) + 3aα-H-4α-acetyl-5α-hydroxy-7aβ-methyl-hexahydro-1-indanone + 3aα-H-4α-<3'-trans acrylic acid>-5α-hydroxy-7aβ-methylhexahydro-1-indanone

Conditions	Yield
at 30℃; for 72h; Nocardia corallina IFO 3338 strain NG-34; Yield given. Yields of byproduct given;
at 30℃; for 72h; Nocardia coralina IFO 3338 strain NG-34; Yield given. Yields of byproduct given;

Soybean sterol → 3aα-H-4α-<3'-propionic acid>-5α-hydroxy-7aβ-methyl-hexahydro-1-indanone-δ-lactone (126784-20-1)

Conditions	Yield
With sorbitan monopalmitate; D-glucose; yeast extract In water at 30℃; for 72h; mutant strain of Nocardia corallina NG-511; Yield given;

3aα-H-4α-<3'-propionic acid>-5α-hydroxy-7aβ-methyl-hexahydro-1-indanone-δ-lactone (126784-20-1) → C13H16O3

Conditions	Yield
Stage #1: 3aα-H-4α-<3'-propionic acid>-5α-hydroxy-7aβ-methyl-hexahydro-1-indanone-δ-lactone With trimethylsilyl trifluoromethanesulfonate; triethylamine In dichloromethane at 0℃; for 3h; Inert atmosphere; Stage #2: With oxygen; palladium diacetate In dimethyl sulfoxide at 60℃; for 3.5h;	75%

3aα-H-4α-<3'-propionic acid>-5α-hydroxy-7aβ-methyl-hexahydro-1-indanone-δ-lactone (126784-20-1) + ethylmagnesium bromide (925-90-6) → (4S,5R,7aS)-5-hydroxy-7a-methyl-4-(3-oxopentyl)octahydro-1H-inden-1-one + (4S,5S,7aS)-5-hydroxy-7a-methyl-4-(3-oxopentyl)octahydro-1H-inden-1-one

Conditions	Yield
In tetrahydrofuran at -40 - -30℃; for 2.16667h; Inert atmosphere;	A n/a B n/a

3aα-H-4α-<3'-propionic acid>-5α-hydroxy-7aβ-methyl-hexahydro-1-indanone-δ-lactone (126784-20-1) → 3aα-H-4α-(3’-propionic acid)-5α-hydroxy-7aβ-methylhexahydro-1-indanedione

Conditions	Yield
With water; sodium hydroxide

3aα-H-4α-<3'-propionic acid>-5α-hydroxy-7aβ-methyl-hexahydro-1-indanone-δ-lactone (126784-20-1) → C14H20O2

Conditions

Yield

Multi-step reaction with 6 steps 1.1: triethylamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3 h / 0 °C / Inert atmosphere 1.2: 3.5 h / 60 °C 2.1: trifluoroacetic acid; sodium tetrahydroborate / dichloromethane / 0.5 h / -10 - 0 °C 3.1: tetrahydrofuran; diethyl ether / 0.33 h / -78 °C / Inert atmosphere 3.2: 4 - 5 h / 40 °C / Inert atmosphere 4.1: samarium diiodide; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 5.1: palladium 10% on activated carbon; hydrogen / methanol / 23 h / 20 °C / 760.05 Torr 5.2: 5 h / Reflux 6.1: toluene-4-sulfonic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 5 h / 100 °C View Scheme

3aα-H-4α-<3'-propionic acid>-5α-hydroxy-7aβ-methyl-hexahydro-1-indanone-δ-lactone (126784-20-1) → C18H26O2 + C18H26O2

Conditions

Yield

Multi-step reaction with 7 steps 1.1: triethylamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3 h / 0 °C / Inert atmosphere 1.2: 3.5 h / 60 °C 2.1: trifluoroacetic acid; sodium tetrahydroborate / dichloromethane / 0.5 h / -10 - 0 °C 3.1: tetrahydrofuran; diethyl ether / 0.33 h / -78 °C / Inert atmosphere 3.2: 4 - 5 h / 40 °C / Inert atmosphere 4.1: samarium diiodide; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 5.1: palladium 10% on activated carbon; hydrogen / methanol / 23 h / 20 °C / 760.05 Torr 5.2: 5 h / Reflux 6.1: toluene-4-sulfonic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 5 h / 100 °C 7.1: potassium tert-butylate / 1,2-dimethoxyethane / 0.25 h / -60 °C 7.2: 2 h / -60 °C View Scheme

3aα-H-4α-<3'-propionic acid>-5α-hydroxy-7aβ-methyl-hexahydro-1-indanone-δ-lactone (126784-20-1) → C18H26O2

Conditions	Yield
Multi-step reaction with 8 steps 1.1: triethylamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3 h / 0 °C / Inert atmosphere 1.2: 3.5 h / 60 °C 2.1: trifluoroacetic acid; sodium tetrahydroborate / dichloromethane / 0.5 h / -10 - 0 °C 3.1: tetrahydrofuran; diethyl ether / 0.33 h / -78 °C / Inert atmosphere 3.2: 4 - 5 h / 40 °C / Inert atmosphere 4.1: samarium diiodide; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 5.1: palladium 10% on activated carbon; hydrogen / methanol / 23 h / 20 °C / 760.05 Torr 5.2: 5 h / Reflux 6.1: toluene-4-sulfonic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 5 h / 100 °C 7.1: potassium tert-butylate / 1,2-dimethoxyethane / 0.25 h / -60 °C 7.2: 2 h / -60 °C 8.1: N-ethyl-N,N-diisopropylamine / ethylene glycol / 2 h / 165 °C View Scheme
Multi-step reaction with 8 steps 1.1: triethylamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3 h / 0 °C / Inert atmosphere 1.2: 3.5 h / 60 °C 2.1: trifluoroacetic acid; sodium tetrahydroborate / dichloromethane / 0.5 h / -10 - 0 °C 3.1: tetrahydrofuran; diethyl ether / 0.33 h / -78 °C / Inert atmosphere 3.2: 4 - 5 h / 40 °C / Inert atmosphere 4.1: samarium diiodide; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 5.1: palladium 10% on activated carbon; hydrogen / methanol / 23 h / 20 °C / 760.05 Torr 5.2: 5 h / Reflux 6.1: toluene-4-sulfonic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 5 h / 100 °C 7.1: potassium tert-butylate / 1,2-dimethoxyethane / 0.25 h / -60 °C 7.2: 2 h / -60 °C 8.1: sodium acetate / 1,2-dichloro-benzene / 2 h / 180 °C View Scheme

3aα-H-4α-<3'-propionic acid>-5α-hydroxy-7aβ-methyl-hexahydro-1-indanone-δ-lactone (126784-20-1) → C18H26O2

Conditions

Yield

Multi-step reaction with 8 steps 1.1: triethylamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3 h / 0 °C / Inert atmosphere 1.2: 3.5 h / 60 °C 2.1: trifluoroacetic acid; sodium tetrahydroborate / dichloromethane / 0.5 h / -10 - 0 °C 3.1: tetrahydrofuran; diethyl ether / 0.33 h / -78 °C / Inert atmosphere 3.2: 4 - 5 h / 40 °C / Inert atmosphere 4.1: samarium diiodide; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 5.1: palladium 10% on activated carbon; hydrogen / methanol / 23 h / 20 °C / 760.05 Torr 5.2: 5 h / Reflux 6.1: toluene-4-sulfonic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 5 h / 100 °C 7.1: potassium tert-butylate / 1,2-dimethoxyethane / 0.25 h / -60 °C 7.2: 2 h / -60 °C 8.1: sodium acetate / 1,2-dichloro-benzene / 2 h / 180 °C View Scheme

3aα-H-4α-<3'-propionic acid>-5α-hydroxy-7aβ-methyl-hexahydro-1-indanone-δ-lactone (126784-20-1) → C18H28O2

Conditions	Yield
Multi-step reaction with 9 steps 1.1: triethylamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3 h / 0 °C / Inert atmosphere 1.2: 3.5 h / 60 °C 2.1: trifluoroacetic acid; sodium tetrahydroborate / dichloromethane / 0.5 h / -10 - 0 °C 3.1: tetrahydrofuran; diethyl ether / 0.33 h / -78 °C / Inert atmosphere 3.2: 4 - 5 h / 40 °C / Inert atmosphere 4.1: samarium diiodide; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 5.1: palladium 10% on activated carbon; hydrogen / methanol / 23 h / 20 °C / 760.05 Torr 5.2: 5 h / Reflux 6.1: toluene-4-sulfonic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 5 h / 100 °C 7.1: potassium tert-butylate / 1,2-dimethoxyethane / 0.25 h / -60 °C 7.2: 2 h / -60 °C 8.1: N-ethyl-N,N-diisopropylamine / ethylene glycol / 2 h / 165 °C 9.1: lithium; ammonia / tetrahydrofuran / -78 °C View Scheme
Multi-step reaction with 9 steps 1.1: triethylamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3 h / 0 °C / Inert atmosphere 1.2: 3.5 h / 60 °C 2.1: trifluoroacetic acid; sodium tetrahydroborate / dichloromethane / 0.5 h / -10 - 0 °C 3.1: tetrahydrofuran; diethyl ether / 0.33 h / -78 °C / Inert atmosphere 3.2: 4 - 5 h / 40 °C / Inert atmosphere 4.1: samarium diiodide; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 5.1: palladium 10% on activated carbon; hydrogen / methanol / 23 h / 20 °C / 760.05 Torr 5.2: 5 h / Reflux 6.1: toluene-4-sulfonic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 5 h / 100 °C 7.1: potassium tert-butylate / 1,2-dimethoxyethane / 0.25 h / -60 °C 7.2: 2 h / -60 °C 8.1: sodium acetate / 1,2-dichloro-benzene / 2 h / 180 °C 9.1: lithium; ammonia / tetrahydrofuran / -78 °C View Scheme

3aα-H-4α-<3'-propionic acid>-5α-hydroxy-7aβ-methyl-hexahydro-1-indanone-δ-lactone (126784-20-1) → C18H30O3

Conditions	Yield
Multi-step reaction with 10 steps 1.1: triethylamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3 h / 0 °C / Inert atmosphere 1.2: 3.5 h / 60 °C 2.1: trifluoroacetic acid; sodium tetrahydroborate / dichloromethane / 0.5 h / -10 - 0 °C 3.1: tetrahydrofuran; diethyl ether / 0.33 h / -78 °C / Inert atmosphere 3.2: 4 - 5 h / 40 °C / Inert atmosphere 4.1: samarium diiodide; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 5.1: palladium 10% on activated carbon; hydrogen / methanol / 23 h / 20 °C / 760.05 Torr 5.2: 5 h / Reflux 6.1: toluene-4-sulfonic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 5 h / 100 °C 7.1: potassium tert-butylate / 1,2-dimethoxyethane / 0.25 h / -60 °C 7.2: 2 h / -60 °C 8.1: N-ethyl-N,N-diisopropylamine / ethylene glycol / 2 h / 165 °C 9.1: lithium; ammonia / tetrahydrofuran / -78 °C 10.1: Wilkinson's catalyst; benzo[1,3,2]dioxaborole / tetrahydrofuran; dichloromethane / 20 h / 20 °C / Inert atmosphere 10.2: 2 h / 0 - 20 °C View Scheme
Multi-step reaction with 10 steps 1.1: triethylamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3 h / 0 °C / Inert atmosphere 1.2: 3.5 h / 60 °C 2.1: trifluoroacetic acid; sodium tetrahydroborate / dichloromethane / 0.5 h / -10 - 0 °C 3.1: tetrahydrofuran; diethyl ether / 0.33 h / -78 °C / Inert atmosphere 3.2: 4 - 5 h / 40 °C / Inert atmosphere 4.1: samarium diiodide; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 5.1: palladium 10% on activated carbon; hydrogen / methanol / 23 h / 20 °C / 760.05 Torr 5.2: 5 h / Reflux 6.1: toluene-4-sulfonic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 5 h / 100 °C 7.1: potassium tert-butylate / 1,2-dimethoxyethane / 0.25 h / -60 °C 7.2: 2 h / -60 °C 8.1: sodium acetate / 1,2-dichloro-benzene / 2 h / 180 °C 9.1: lithium; ammonia / tetrahydrofuran / -78 °C 10.1: Wilkinson's catalyst; benzo[1,3,2]dioxaborole / tetrahydrofuran; dichloromethane / 20 h / 20 °C / Inert atmosphere 10.2: 2 h / 0 - 20 °C View Scheme

3aα-H-4α-<3'-propionic acid>-5α-hydroxy-7aβ-methyl-hexahydro-1-indanone-δ-lactone (126784-20-1) → C18H30O3 + C18H30O3

Conditions	Yield
Multi-step reaction with 10 steps 1.1: triethylamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3 h / 0 °C / Inert atmosphere 1.2: 3.5 h / 60 °C 2.1: trifluoroacetic acid; sodium tetrahydroborate / dichloromethane / 0.5 h / -10 - 0 °C 3.1: tetrahydrofuran; diethyl ether / 0.33 h / -78 °C / Inert atmosphere 3.2: 4 - 5 h / 40 °C / Inert atmosphere 4.1: samarium diiodide; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 5.1: palladium 10% on activated carbon; hydrogen / methanol / 23 h / 20 °C / 760.05 Torr 5.2: 5 h / Reflux 6.1: toluene-4-sulfonic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 5 h / 100 °C 7.1: potassium tert-butylate / 1,2-dimethoxyethane / 0.25 h / -60 °C 7.2: 2 h / -60 °C 8.1: N-ethyl-N,N-diisopropylamine / ethylene glycol / 2 h / 165 °C 9.1: lithium; ammonia / tetrahydrofuran / -78 °C 10.1: Wilkinson's catalyst; benzo[1,3,2]dioxaborole / tetrahydrofuran; dichloromethane / 20 h / 20 °C / Inert atmosphere 10.2: 2 h / 0 - 20 °C View Scheme
Multi-step reaction with 10 steps 1.1: triethylamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3 h / 0 °C / Inert atmosphere 1.2: 3.5 h / 60 °C 2.1: trifluoroacetic acid; sodium tetrahydroborate / dichloromethane / 0.5 h / -10 - 0 °C 3.1: tetrahydrofuran; diethyl ether / 0.33 h / -78 °C / Inert atmosphere 3.2: 4 - 5 h / 40 °C / Inert atmosphere 4.1: samarium diiodide; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 5.1: palladium 10% on activated carbon; hydrogen / methanol / 23 h / 20 °C / 760.05 Torr 5.2: 5 h / Reflux 6.1: toluene-4-sulfonic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 5 h / 100 °C 7.1: potassium tert-butylate / 1,2-dimethoxyethane / 0.25 h / -60 °C 7.2: 2 h / -60 °C 8.1: sodium acetate / 1,2-dichloro-benzene / 2 h / 180 °C 9.1: lithium; ammonia / tetrahydrofuran / -78 °C 10.1: Wilkinson's catalyst; benzo[1,3,2]dioxaborole / tetrahydrofuran; dichloromethane / 20 h / 20 °C / Inert atmosphere 10.2: 2 h / 0 - 20 °C View Scheme

3aα-H-4α-<3'-propionic acid>-5α-hydroxy-7aβ-methyl-hexahydro-1-indanone-δ-lactone (126784-20-1) → C18H29IO2

Conditions	Yield
Multi-step reaction with 10 steps 1.1: triethylamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3 h / 0 °C / Inert atmosphere 1.2: 3.5 h / 60 °C 2.1: trifluoroacetic acid; sodium tetrahydroborate / dichloromethane / 0.5 h / -10 - 0 °C 3.1: tetrahydrofuran; diethyl ether / 0.33 h / -78 °C / Inert atmosphere 3.2: 4 - 5 h / 40 °C / Inert atmosphere 4.1: samarium diiodide; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 5.1: palladium 10% on activated carbon; hydrogen / methanol / 23 h / 20 °C / 760.05 Torr 5.2: 5 h / Reflux 6.1: toluene-4-sulfonic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 5 h / 100 °C 7.1: potassium tert-butylate / 1,2-dimethoxyethane / 0.25 h / -60 °C 7.2: 2 h / -60 °C 8.1: N-ethyl-N,N-diisopropylamine / ethylene glycol / 2 h / 165 °C 9.1: lithium; ammonia / tetrahydrofuran / -78 °C 10.1: Wilkinson's catalyst; benzo[1,3,2]dioxaborole / tetrahydrofuran; dichloromethane / 20 h / 20 °C / Inert atmosphere 10.2: 2 h / 0 - 20 °C View Scheme
Multi-step reaction with 10 steps 1.1: triethylamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3 h / 0 °C / Inert atmosphere 1.2: 3.5 h / 60 °C 2.1: trifluoroacetic acid; sodium tetrahydroborate / dichloromethane / 0.5 h / -10 - 0 °C 3.1: tetrahydrofuran; diethyl ether / 0.33 h / -78 °C / Inert atmosphere 3.2: 4 - 5 h / 40 °C / Inert atmosphere 4.1: samarium diiodide; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 5.1: palladium 10% on activated carbon; hydrogen / methanol / 23 h / 20 °C / 760.05 Torr 5.2: 5 h / Reflux 6.1: toluene-4-sulfonic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 5 h / 100 °C 7.1: potassium tert-butylate / 1,2-dimethoxyethane / 0.25 h / -60 °C 7.2: 2 h / -60 °C 8.1: sodium acetate / 1,2-dichloro-benzene / 2 h / 180 °C 9.1: lithium; ammonia / tetrahydrofuran / -78 °C 10.1: Wilkinson's catalyst; benzo[1,3,2]dioxaborole / tetrahydrofuran; dichloromethane / 20 h / 20 °C / Inert atmosphere 10.2: 2 h / 0 - 20 °C View Scheme

3aα-H-4α-<3'-propionic acid>-5α-hydroxy-7aβ-methyl-hexahydro-1-indanone-δ-lactone (126784-20-1) → C18H28O2

Conditions	Yield
Multi-step reaction with 11 steps 1.1: triethylamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3 h / 0 °C / Inert atmosphere 1.2: 3.5 h / 60 °C 2.1: trifluoroacetic acid; sodium tetrahydroborate / dichloromethane / 0.5 h / -10 - 0 °C 3.1: tetrahydrofuran; diethyl ether / 0.33 h / -78 °C / Inert atmosphere 3.2: 4 - 5 h / 40 °C / Inert atmosphere 4.1: samarium diiodide; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 5.1: palladium 10% on activated carbon; hydrogen / methanol / 23 h / 20 °C / 760.05 Torr 5.2: 5 h / Reflux 6.1: toluene-4-sulfonic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 5 h / 100 °C 7.1: potassium tert-butylate / 1,2-dimethoxyethane / 0.25 h / -60 °C 7.2: 2 h / -60 °C 8.1: N-ethyl-N,N-diisopropylamine / ethylene glycol / 2 h / 165 °C 9.1: lithium; ammonia / tetrahydrofuran / -78 °C 10.1: Wilkinson's catalyst; benzo[1,3,2]dioxaborole / tetrahydrofuran; dichloromethane / 20 h / 20 °C / Inert atmosphere 10.2: 2 h / 0 - 20 °C 11.1: 1-(Trimethylsilyl)imidazole; 1,1,1,3,3,3-hexamethyl-disilazane / dichloromethane / 2 h / 20 - 40 °C 11.2: 3 h / 20 °C 11.3: 4 h / 20 °C View Scheme
Multi-step reaction with 11 steps 1.1: triethylamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3 h / 0 °C / Inert atmosphere 1.2: 3.5 h / 60 °C 2.1: trifluoroacetic acid; sodium tetrahydroborate / dichloromethane / 0.5 h / -10 - 0 °C 3.1: tetrahydrofuran; diethyl ether / 0.33 h / -78 °C / Inert atmosphere 3.2: 4 - 5 h / 40 °C / Inert atmosphere 4.1: samarium diiodide; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 5.1: palladium 10% on activated carbon; hydrogen / methanol / 23 h / 20 °C / 760.05 Torr 5.2: 5 h / Reflux 6.1: toluene-4-sulfonic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 5 h / 100 °C 7.1: potassium tert-butylate / 1,2-dimethoxyethane / 0.25 h / -60 °C 7.2: 2 h / -60 °C 8.1: sodium acetate / 1,2-dichloro-benzene / 2 h / 180 °C 9.1: lithium; ammonia / tetrahydrofuran / -78 °C 10.1: Wilkinson's catalyst; benzo[1,3,2]dioxaborole / tetrahydrofuran; dichloromethane / 20 h / 20 °C / Inert atmosphere 10.2: 2 h / 0 - 20 °C 11.1: 1-(Trimethylsilyl)imidazole; 1,1,1,3,3,3-hexamethyl-disilazane / dichloromethane / 2 h / 20 - 40 °C 11.2: 3 h / 20 °C 11.3: 4 h / 20 °C View Scheme

3aα-H-4α-<3'-propionic acid>-5α-hydroxy-7aβ-methyl-hexahydro-1-indanone-δ-lactone (126784-20-1) → C19H30O

Conditions	Yield
Multi-step reaction with 12 steps 1.1: triethylamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3 h / 0 °C / Inert atmosphere 1.2: 3.5 h / 60 °C 2.1: trifluoroacetic acid; sodium tetrahydroborate / dichloromethane / 0.5 h / -10 - 0 °C 3.1: tetrahydrofuran; diethyl ether / 0.33 h / -78 °C / Inert atmosphere 3.2: 4 - 5 h / 40 °C / Inert atmosphere 4.1: samarium diiodide; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 5.1: palladium 10% on activated carbon; hydrogen / methanol / 23 h / 20 °C / 760.05 Torr 5.2: 5 h / Reflux 6.1: toluene-4-sulfonic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 5 h / 100 °C 7.1: potassium tert-butylate / 1,2-dimethoxyethane / 0.25 h / -60 °C 7.2: 2 h / -60 °C 8.1: N-ethyl-N,N-diisopropylamine / ethylene glycol / 2 h / 165 °C 9.1: lithium; ammonia / tetrahydrofuran / -78 °C 10.1: Wilkinson's catalyst; benzo[1,3,2]dioxaborole / tetrahydrofuran; dichloromethane / 20 h / 20 °C / Inert atmosphere 10.2: 2 h / 0 - 20 °C 11.1: 1-(Trimethylsilyl)imidazole; 1,1,1,3,3,3-hexamethyl-disilazane / dichloromethane / 2 h / 20 - 40 °C 11.2: 3 h / 20 °C 11.3: 4 h / 20 °C 12.1: zinc; lead(II) chloride / tetrahydrofuran / 0.5 h / 0 °C 12.2: 0.5 h / 0 - 20 °C 12.3: 2 h / 0 °C View Scheme
Multi-step reaction with 12 steps 1.1: triethylamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3 h / 0 °C / Inert atmosphere 1.2: 3.5 h / 60 °C 2.1: trifluoroacetic acid; sodium tetrahydroborate / dichloromethane / 0.5 h / -10 - 0 °C 3.1: tetrahydrofuran; diethyl ether / 0.33 h / -78 °C / Inert atmosphere 3.2: 4 - 5 h / 40 °C / Inert atmosphere 4.1: samarium diiodide; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 5.1: palladium 10% on activated carbon; hydrogen / methanol / 23 h / 20 °C / 760.05 Torr 5.2: 5 h / Reflux 6.1: toluene-4-sulfonic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 5 h / 100 °C 7.1: potassium tert-butylate / 1,2-dimethoxyethane / 0.25 h / -60 °C 7.2: 2 h / -60 °C 8.1: sodium acetate / 1,2-dichloro-benzene / 2 h / 180 °C 9.1: lithium; ammonia / tetrahydrofuran / -78 °C 10.1: Wilkinson's catalyst; benzo[1,3,2]dioxaborole / tetrahydrofuran; dichloromethane / 20 h / 20 °C / Inert atmosphere 10.2: 2 h / 0 - 20 °C 11.1: 1-(Trimethylsilyl)imidazole; 1,1,1,3,3,3-hexamethyl-disilazane / dichloromethane / 2 h / 20 - 40 °C 11.2: 3 h / 20 °C 11.3: 4 h / 20 °C 12.1: zinc; lead(II) chloride / tetrahydrofuran / 0.5 h / 0 °C 12.2: 0.5 h / 0 - 20 °C 12.3: 2 h / 0 °C View Scheme

3aα-H-4α-<3'-propionic acid>-5α-hydroxy-7aβ-methyl-hexahydro-1-indanone-δ-lactone (126784-20-1) → C20H32O

Conditions	Yield
Multi-step reaction with 13 steps 1.1: triethylamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3 h / 0 °C / Inert atmosphere 1.2: 3.5 h / 60 °C 2.1: trifluoroacetic acid; sodium tetrahydroborate / dichloromethane / 0.5 h / -10 - 0 °C 3.1: tetrahydrofuran; diethyl ether / 0.33 h / -78 °C / Inert atmosphere 3.2: 4 - 5 h / 40 °C / Inert atmosphere 4.1: samarium diiodide; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 5.1: palladium 10% on activated carbon; hydrogen / methanol / 23 h / 20 °C / 760.05 Torr 5.2: 5 h / Reflux 6.1: toluene-4-sulfonic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 5 h / 100 °C 7.1: potassium tert-butylate / 1,2-dimethoxyethane / 0.25 h / -60 °C 7.2: 2 h / -60 °C 8.1: N-ethyl-N,N-diisopropylamine / ethylene glycol / 2 h / 165 °C 9.1: lithium; ammonia / tetrahydrofuran / -78 °C 10.1: Wilkinson's catalyst; benzo[1,3,2]dioxaborole / tetrahydrofuran; dichloromethane / 20 h / 20 °C / Inert atmosphere 10.2: 2 h / 0 - 20 °C 11.1: 1-(Trimethylsilyl)imidazole; 1,1,1,3,3,3-hexamethyl-disilazane / dichloromethane / 2 h / 20 - 40 °C 11.2: 3 h / 20 °C 11.3: 4 h / 20 °C 12.1: zinc; lead(II) chloride / tetrahydrofuran / 0.5 h / 0 °C 12.2: 0.5 h / 0 - 20 °C 12.3: 2 h / 0 °C 13.1: trifluoroacetic acid; diethylzinc / hexane; dichloromethane / 0.33 h / Inert atmosphere 13.2: 12 h / 20 °C View Scheme
Multi-step reaction with 13 steps 1.1: triethylamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3 h / 0 °C / Inert atmosphere 1.2: 3.5 h / 60 °C 2.1: trifluoroacetic acid; sodium tetrahydroborate / dichloromethane / 0.5 h / -10 - 0 °C 3.1: tetrahydrofuran; diethyl ether / 0.33 h / -78 °C / Inert atmosphere 3.2: 4 - 5 h / 40 °C / Inert atmosphere 4.1: samarium diiodide; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 5.1: palladium 10% on activated carbon; hydrogen / methanol / 23 h / 20 °C / 760.05 Torr 5.2: 5 h / Reflux 6.1: toluene-4-sulfonic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 5 h / 100 °C 7.1: potassium tert-butylate / 1,2-dimethoxyethane / 0.25 h / -60 °C 7.2: 2 h / -60 °C 8.1: sodium acetate / 1,2-dichloro-benzene / 2 h / 180 °C 9.1: lithium; ammonia / tetrahydrofuran / -78 °C 10.1: Wilkinson's catalyst; benzo[1,3,2]dioxaborole / tetrahydrofuran; dichloromethane / 20 h / 20 °C / Inert atmosphere 10.2: 2 h / 0 - 20 °C 11.1: 1-(Trimethylsilyl)imidazole; 1,1,1,3,3,3-hexamethyl-disilazane / dichloromethane / 2 h / 20 - 40 °C 11.2: 3 h / 20 °C 11.3: 4 h / 20 °C 12.1: zinc; lead(II) chloride / tetrahydrofuran / 0.5 h / 0 °C 12.2: 0.5 h / 0 - 20 °C 12.3: 2 h / 0 °C 13.1: trifluoroacetic acid; diethylzinc / hexane; dichloromethane / 0.33 h / Inert atmosphere 13.2: 12 h / 20 °C View Scheme

3aα-H-4α-<3'-propionic acid>-5α-hydroxy-7aβ-methyl-hexahydro-1-indanone-δ-lactone (126784-20-1) → wickerol A

Conditions	Yield
Multi-step reaction with 14 steps 1.1: triethylamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3 h / 0 °C / Inert atmosphere 1.2: 3.5 h / 60 °C 2.1: trifluoroacetic acid; sodium tetrahydroborate / dichloromethane / 0.5 h / -10 - 0 °C 3.1: tetrahydrofuran; diethyl ether / 0.33 h / -78 °C / Inert atmosphere 3.2: 4 - 5 h / 40 °C / Inert atmosphere 4.1: samarium diiodide; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 5.1: palladium 10% on activated carbon; hydrogen / methanol / 23 h / 20 °C / 760.05 Torr 5.2: 5 h / Reflux 6.1: toluene-4-sulfonic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 5 h / 100 °C 7.1: potassium tert-butylate / 1,2-dimethoxyethane / 0.25 h / -60 °C 7.2: 2 h / -60 °C 8.1: N-ethyl-N,N-diisopropylamine / ethylene glycol / 2 h / 165 °C 9.1: lithium; ammonia / tetrahydrofuran / -78 °C 10.1: Wilkinson's catalyst; benzo[1,3,2]dioxaborole / tetrahydrofuran; dichloromethane / 20 h / 20 °C / Inert atmosphere 10.2: 2 h / 0 - 20 °C 11.1: 1-(Trimethylsilyl)imidazole; 1,1,1,3,3,3-hexamethyl-disilazane / dichloromethane / 2 h / 20 - 40 °C 11.2: 3 h / 20 °C 11.3: 4 h / 20 °C 12.1: zinc; lead(II) chloride / tetrahydrofuran / 0.5 h / 0 °C 12.2: 0.5 h / 0 - 20 °C 12.3: 2 h / 0 °C 13.1: trifluoroacetic acid; diethylzinc / hexane; dichloromethane / 0.33 h / Inert atmosphere 13.2: 12 h / 20 °C 14.1: hydrogen; platinum(IV) oxide / acetic acid / 48 h / 60 °C / 38002.6 Torr View Scheme
Multi-step reaction with 14 steps 1.1: triethylamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3 h / 0 °C / Inert atmosphere 1.2: 3.5 h / 60 °C 2.1: trifluoroacetic acid; sodium tetrahydroborate / dichloromethane / 0.5 h / -10 - 0 °C 3.1: tetrahydrofuran; diethyl ether / 0.33 h / -78 °C / Inert atmosphere 3.2: 4 - 5 h / 40 °C / Inert atmosphere 4.1: samarium diiodide; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 5.1: palladium 10% on activated carbon; hydrogen / methanol / 23 h / 20 °C / 760.05 Torr 5.2: 5 h / Reflux 6.1: toluene-4-sulfonic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 5 h / 100 °C 7.1: potassium tert-butylate / 1,2-dimethoxyethane / 0.25 h / -60 °C 7.2: 2 h / -60 °C 8.1: sodium acetate / 1,2-dichloro-benzene / 2 h / 180 °C 9.1: lithium; ammonia / tetrahydrofuran / -78 °C 10.1: Wilkinson's catalyst; benzo[1,3,2]dioxaborole / tetrahydrofuran; dichloromethane / 20 h / 20 °C / Inert atmosphere 10.2: 2 h / 0 - 20 °C 11.1: 1-(Trimethylsilyl)imidazole; 1,1,1,3,3,3-hexamethyl-disilazane / dichloromethane / 2 h / 20 - 40 °C 11.2: 3 h / 20 °C 11.3: 4 h / 20 °C 12.1: zinc; lead(II) chloride / tetrahydrofuran / 0.5 h / 0 °C 12.2: 0.5 h / 0 - 20 °C 12.3: 2 h / 0 °C 13.1: trifluoroacetic acid; diethylzinc / hexane; dichloromethane / 0.33 h / Inert atmosphere 13.2: 12 h / 20 °C 14.1: hydrogen; platinum(IV) oxide / acetic acid / 48 h / 60 °C / 38002.6 Torr View Scheme

Upstream product

• 83-46-5 β-sitosterol 
• 57-88-5 cholesterol 
• 601-57-0 Cholest-4-en-3-one 
• 57-83-0 progesterone 
• 80-97-7 Cholestanol 
• 81-25-4 cholic acid 
• 434-13-9 Lithocholic acid 
• 57-83-0 Progesterone 
• 257939-67-6 24-ethylcholesterol 
• 83-44-3 Deoxycholic acid 

Relevant articles and documents

Microbial degradation of steroids to hexahydroindanone derivatives

-

DEOXYCHOLIC ACID DEGRADATION BY A PSEUDOMONAS SP: PHENOLIC AND NEUTRAL PRODUCTS

The microbial degradation of deoxycholic acid by Pseudomonas sp.MR108 was studied, and four products were isolated.Evidence is presented that one is the phenol 3,12β-dihydroxy-9,10-secoandrosta-1,3,5(10)-trien-9,17-dione (11) and that the other three are the neutral compounds 3aαH-4α--5α-hydroxy-7aβ-methyl-hexahydro-1-indanone-δ-lactone (12), 12β-hydroxyandrosta-1,4-dien-3,17-dione (10), and 12α-hydroxyandrosta-1,4-dien-3,17-dione (7).