Synthesis of polyhydroxysterols (III): synthesis and structural elucidation of 24-methylenecholest-4-en-3 beta,6 alpha-diol

Using stigmasterol as the starting material, 24-methylenecholest-4-en-3beta,6alpha-diol (2) was synthesized in eight steps in 13% overall yield. The introduction of the sterol side-chain was carried out using (3-methyl-2-oxobutyl)-triphenylarsonium bromide (11) and K2CO3 in a solid-liquid phase-tran...

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Bibliographic Details
Published inSteroids Vol. 67; no. 13-14; pp. 1015 - 1019
Main Authors Cui, JG, Lin, CW, Zeng, LM, Su, JY
Format Journal Article
LanguageEnglish
Published NEW YORK Elsevier 01.12.2002
Subjects
Biochemistry & Molecular Biology
Endocrinology & Metabolism
Life Sciences & Biomedicine
Science & Technology
steroid synthesis
solid-liquid phase-transfer Wittig reaction
polyhydroxylated sterol
STEROL
24-methylenecholest-4-en-3 beta,6 alpha-diol
PYRIDINIUM CHLOROCHROMATE
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Summary:Using stigmasterol as the starting material, 24-methylenecholest-4-en-3beta,6alpha-diol (2) was synthesized in eight steps in 13% overall yield. The introduction of the sterol side-chain was carried out using (3-methyl-2-oxobutyl)-triphenylarsonium bromide (11) and K2CO3 in a solid-liquid phase-transfer Wittig reaction. Construction of the steroidal nucleus was finished by oxidation of 24-methylenecholest-5-en-3beta-ol (9) with pyridinium chlorochromate (PCC) in dichloromethane at ambient temperature and by reduction of 24-methylenecholest-4-en-3,6-dione (10) with NaBH4 in the presence of CeCl3.7H(2)O. (C) 2002 Elsevier Science Inc. All rights reserved.
ISSN:0039-128X
DOI:10.1016/S0039-128X(02)00059-4