Synthesis of (23R)- and (23S)-Methylcholesterol

Hui Ting Li; Ian J. Massey; Dale C. Swenson; William L. Duax; Carl Djerassi

doi:10.1021/jo00149a010

Synthesis of (23R)- and (23S)-Methylcholesterol

Hui Ting Li
, Ian J. Massey
, Dale C. Swenson
, William L. Duax
, Carl Djerassi

Department of Structural Biology

Stanford University
Hauptman-Woodward Medical Research Institute, Inc.

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

12 Scopus citations

Abstract

23-Methylcholesterol is likely to exist in nature. In order to facilitate its recognition, (231?)- and (23S)-methylcholesterol have been synthesized, and the absolute configuration has been established by X-ray analysis. Substantial differences were encountered in comparing the course of catalytic hydrogenation and of double-bond isomerization of 22- and 23-methylenecholesterol.

Original language	English
Pages (from-to)	48-54
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	48
Issue number	1
DOIs	https://doi.org/10.1021/jo00149a010
State	Published - Jan 1983

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title = "Synthesis of (23R)- and (23S)-Methylcholesterol",

abstract = "23-Methylcholesterol is likely to exist in nature. In order to facilitate its recognition, (231?)- and (23S)-methylcholesterol have been synthesized, and the absolute configuration has been established by X-ray analysis. Substantial differences were encountered in comparing the course of catalytic hydrogenation and of double-bond isomerization of 22- and 23-methylenecholesterol.",

author = "Li, \{Hui Ting\} and Massey, \{Ian J.\} and Swenson, \{Dale C.\} and Duax, \{William L.\} and Carl Djerassi",

year = "1983",

month = jan,

doi = "10.1021/jo00149a010",

language = "English",

volume = "48",

pages = "48--54",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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T1 - Synthesis of (23R)- and (23S)-Methylcholesterol

AU - Li, Hui Ting

AU - Massey, Ian J.

AU - Swenson, Dale C.

AU - Duax, William L.

AU - Djerassi, Carl

PY - 1983/1

Y1 - 1983/1

N2 - 23-Methylcholesterol is likely to exist in nature. In order to facilitate its recognition, (231?)- and (23S)-methylcholesterol have been synthesized, and the absolute configuration has been established by X-ray analysis. Substantial differences were encountered in comparing the course of catalytic hydrogenation and of double-bond isomerization of 22- and 23-methylenecholesterol.

AB - 23-Methylcholesterol is likely to exist in nature. In order to facilitate its recognition, (231?)- and (23S)-methylcholesterol have been synthesized, and the absolute configuration has been established by X-ray analysis. Substantial differences were encountered in comparing the course of catalytic hydrogenation and of double-bond isomerization of 22- and 23-methylenecholesterol.

UR - https://www.scopus.com/pages/publications/0041082482

U2 - 10.1021/jo00149a010

DO - 10.1021/jo00149a010

M3 - Article

AN - SCOPUS:0041082482

SN - 0022-3263

VL - 48

SP - 48

EP - 54

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 1

ER -

Synthesis of (23R)- and (23S)-Methylcholesterol

Abstract

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