The microbiological hydroxylation of 3,16-disubstituted androstanes by Cephalosporium aphidicola

James R. Hanson; Peter B. Hitchcock; A. Christy Hunter

doi:10.1016/S0031-9422(98)00096-X

The microbiological hydroxylation of 3,16-disubstituted androstanes by Cephalosporium aphidicola

James R. Hanson
, Peter B. Hitchcock
, A. Christy Hunter

Research output: Contribution to journal › Article › peer-review

Abstract

5α-Androstane-3, 16-dione has been prepared by hydroboration and oxidation of 3β-hydroxy-5α-androst-16-ene. Reduction with sodium borohydride gave the 3β, 16β-diol. The fungus Cephalosporium aphidicola has been shown to hydroxylate 5α-androstane-3, 16-dione predominantly at the C- 6β position with minor hydroxylation occurring at the C-7α and C-14α positions. In contrast hydroxylation of the 3β, 16β-diol took place at C- 11α. The 3β-hydroxy-16α, 17α-epoxide was hydroxylated at the C-6β position.

Original language	English
Pages (from-to)	1287-1292
Number of pages	5
Journal	Phytochemistry
Volume	49
Issue number	5
DOIs	https://doi.org/10.1016/S0031-9422(98)00096-X
Publication status	Published - 5 Nov 1998

Keywords

16-dione
5α- androstane-3
Cephalosporium aphidicola
Microbiological hydroxylation
Steroid

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10.1016/S0031-9422(98)00096-X

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title = "The microbiological hydroxylation of 3,16-disubstituted androstanes by Cephalosporium aphidicola",

abstract = "5α-Androstane-3, 16-dione has been prepared by hydroboration and oxidation of 3β-hydroxy-5α-androst-16-ene. Reduction with sodium borohydride gave the 3β, 16β-diol. The fungus Cephalosporium aphidicola has been shown to hydroxylate 5α-androstane-3, 16-dione predominantly at the C- 6β position with minor hydroxylation occurring at the C-7α and C-14α positions. In contrast hydroxylation of the 3β, 16β-diol took place at C- 11α. The 3β-hydroxy-16α, 17α-epoxide was hydroxylated at the C-6β position.",

keywords = "16-dione, 5α- androstane-3, Cephalosporium aphidicola, Microbiological hydroxylation, Steroid",

author = "Hanson, \{James R.\} and Hitchcock, \{Peter B.\} and Hunter, \{A. Christy\}",

year = "1998",

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doi = "10.1016/S0031-9422(98)00096-X",

language = "English",

volume = "49",

pages = "1287--1292",

journal = "Phytochemistry",

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TY - JOUR

T1 - The microbiological hydroxylation of 3,16-disubstituted androstanes by Cephalosporium aphidicola

AU - Hanson, James R.

AU - Hitchcock, Peter B.

AU - Hunter, A. Christy

PY - 1998/11/5

Y1 - 1998/11/5

N2 - 5α-Androstane-3, 16-dione has been prepared by hydroboration and oxidation of 3β-hydroxy-5α-androst-16-ene. Reduction with sodium borohydride gave the 3β, 16β-diol. The fungus Cephalosporium aphidicola has been shown to hydroxylate 5α-androstane-3, 16-dione predominantly at the C- 6β position with minor hydroxylation occurring at the C-7α and C-14α positions. In contrast hydroxylation of the 3β, 16β-diol took place at C- 11α. The 3β-hydroxy-16α, 17α-epoxide was hydroxylated at the C-6β position.

AB - 5α-Androstane-3, 16-dione has been prepared by hydroboration and oxidation of 3β-hydroxy-5α-androst-16-ene. Reduction with sodium borohydride gave the 3β, 16β-diol. The fungus Cephalosporium aphidicola has been shown to hydroxylate 5α-androstane-3, 16-dione predominantly at the C- 6β position with minor hydroxylation occurring at the C-7α and C-14α positions. In contrast hydroxylation of the 3β, 16β-diol took place at C- 11α. The 3β-hydroxy-16α, 17α-epoxide was hydroxylated at the C-6β position.

KW - 16-dione

KW - 5α- androstane-3

KW - Cephalosporium aphidicola

KW - Microbiological hydroxylation

KW - Steroid

U2 - 10.1016/S0031-9422(98)00096-X

DO - 10.1016/S0031-9422(98)00096-X

M3 - Article

SN - 0031-9422

VL - 49

SP - 1287

EP - 1292

JO - Phytochemistry

JF - Phytochemistry

IS - 5

ER -

The microbiological hydroxylation of 3,16-disubstituted androstanes by Cephalosporium aphidicola

Abstract

Keywords

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