Stereochemistry of the reduction of 3β-benzoyloxycholest-5-en-4-one with sodium borohydride

Antoinette Viger; Andrée Marquet; Derek H.R. Barton; William B. Motherwell; Samir Z. Zard

doi:10.1039/p19820001937

Stereochemistry of the reduction of 3β-benzoyloxycholest-5-en-4-one with sodium borohydride

Antoinette Viger, Andrée Marquet, Derek H.R. Barton, William B. Motherwell, Samir Z. Zard

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

Abstract

Reduction of 3β-benzoyloxycholest-5-en-4-one (3) with sodium borohydride under various conditions affords only minor amounts of 3β-benzoyloxycholest-5-en-4β-ol (2a). The major product is the 4α-isomer (6). Using sodium borodeuteride it has been shown that the 3β-benzoyloxycholest-5-en-4β-ol obtained is deuteriated at the 3α-position in relatively alkaline conditions, but at 4α- under conditions near neutrality. A plausible mechanism has been proposed for this interesting result.

Original language	English
Pages (from-to)	1937-1940
Number of pages	4
Journal	Journal of the Chemical Society. Perkin Transactions 1
DOIs	https://doi.org/10.1039/p19820001937
Publication status	Published - 1 Jan 1982
Externally published	Yes

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title = "Stereochemistry of the reduction of 3β-benzoyloxycholest-5-en-4-one with sodium borohydride",

abstract = "Reduction of 3β-benzoyloxycholest-5-en-4-one (3) with sodium borohydride under various conditions affords only minor amounts of 3β-benzoyloxycholest-5-en-4β-ol (2a). The major product is the 4α-isomer (6). Using sodium borodeuteride it has been shown that the 3β-benzoyloxycholest-5-en-4β-ol obtained is deuteriated at the 3α-position in relatively alkaline conditions, but at 4α- under conditions near neutrality. A plausible mechanism has been proposed for this interesting result.",

author = "Antoinette Viger and Andr{\'e}e Marquet and Barton, \{Derek H.R.\} and Motherwell, \{William B.\} and Zard, \{Samir Z.\}",

year = "1982",

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doi = "10.1039/p19820001937",

language = "English",

pages = "1937--1940",

journal = "Journal of the Chemical Society. Perkin Transactions 1",

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T1 - Stereochemistry of the reduction of 3β-benzoyloxycholest-5-en-4-one with sodium borohydride

AU - Viger, Antoinette

AU - Marquet, Andrée

AU - Barton, Derek H.R.

AU - Motherwell, William B.

AU - Zard, Samir Z.

PY - 1982/1/1

Y1 - 1982/1/1

N2 - Reduction of 3β-benzoyloxycholest-5-en-4-one (3) with sodium borohydride under various conditions affords only minor amounts of 3β-benzoyloxycholest-5-en-4β-ol (2a). The major product is the 4α-isomer (6). Using sodium borodeuteride it has been shown that the 3β-benzoyloxycholest-5-en-4β-ol obtained is deuteriated at the 3α-position in relatively alkaline conditions, but at 4α- under conditions near neutrality. A plausible mechanism has been proposed for this interesting result.

AB - Reduction of 3β-benzoyloxycholest-5-en-4-one (3) with sodium borohydride under various conditions affords only minor amounts of 3β-benzoyloxycholest-5-en-4β-ol (2a). The major product is the 4α-isomer (6). Using sodium borodeuteride it has been shown that the 3β-benzoyloxycholest-5-en-4β-ol obtained is deuteriated at the 3α-position in relatively alkaline conditions, but at 4α- under conditions near neutrality. A plausible mechanism has been proposed for this interesting result.

U2 - 10.1039/p19820001937

DO - 10.1039/p19820001937

M3 - Article

AN - SCOPUS:37049104986

SN - 1472-7781

SP - 1937

EP - 1940

JO - Journal of the Chemical Society. Perkin Transactions 1

JF - Journal of the Chemical Society. Perkin Transactions 1

ER -

Stereochemistry of the reduction of 3β-benzoyloxycholest-5-en-4-one with sodium borohydride

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