A very short degradation of the bile acid side chain

Derek H.R. Barton; Jocelyne Wozniak; Samir Z. Zard

doi:10.1039/C39870001383

A very short degradation of the bile acid side chain

Derek H.R. Barton
, Jocelyne Wozniak
, Samir Z. Zard

Centre national de la recherche scientifique
Department of Chemistry
Texas A&M University
Laboratoire de Synthèse Organique

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

10 Citations (Scopus)

Abstract

Reaction of the cholanic acid derivative (1) with thionyl chloride and pyridine gave, after quenching with methanol, the α-sulphine ester (3); treatment with acetic anhydride-sulphuric acid afforded the keto ester (5) which, on exposure to air in the presence of copper(II) ions and base, gave the 20-keto pregnane derivative (9) in excellent overall yield.

Original language	English
Pages (from-to)	1383-1385
Number of pages	3
Journal	Journal of the Chemical Society, Chemical Communications
Issue number	18
DOIs	https://doi.org/10.1039/C39870001383
Publication status	Published - 1 Dec 1987

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title = "A very short degradation of the bile acid side chain",

abstract = "Reaction of the cholanic acid derivative (1) with thionyl chloride and pyridine gave, after quenching with methanol, the α-sulphine ester (3); treatment with acetic anhydride-sulphuric acid afforded the keto ester (5) which, on exposure to air in the presence of copper(II) ions and base, gave the 20-keto pregnane derivative (9) in excellent overall yield.",

author = "Barton, \{Derek H.R.\} and Jocelyne Wozniak and Zard, \{Samir Z.\}",

year = "1987",

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doi = "10.1039/C39870001383",

language = "English",

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journal = "Journal of the Chemical Society, Chemical Communications",

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T1 - A very short degradation of the bile acid side chain

AU - Barton, Derek H.R.

AU - Wozniak, Jocelyne

AU - Zard, Samir Z.

PY - 1987/12/1

Y1 - 1987/12/1

N2 - Reaction of the cholanic acid derivative (1) with thionyl chloride and pyridine gave, after quenching with methanol, the α-sulphine ester (3); treatment with acetic anhydride-sulphuric acid afforded the keto ester (5) which, on exposure to air in the presence of copper(II) ions and base, gave the 20-keto pregnane derivative (9) in excellent overall yield.

AB - Reaction of the cholanic acid derivative (1) with thionyl chloride and pyridine gave, after quenching with methanol, the α-sulphine ester (3); treatment with acetic anhydride-sulphuric acid afforded the keto ester (5) which, on exposure to air in the presence of copper(II) ions and base, gave the 20-keto pregnane derivative (9) in excellent overall yield.

U2 - 10.1039/C39870001383

DO - 10.1039/C39870001383

M3 - Article

AN - SCOPUS:37049068412

SN - 0022-4936

SP - 1383

EP - 1385

JO - Journal of the Chemical Society, Chemical Communications

JF - Journal of the Chemical Society, Chemical Communications

IS - 18

ER -

A very short degradation of the bile acid side chain

Abstract

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