The Journal of Organic Chemistry

Scope and regiochemical control of the allylpotassium reaction in the synthesis of sterols with unsaturated side chains

JL Giner, C Margot, C Djerassi

Index: Giner, Jose-Luis; Margot, Christian; Djerassi, Carl Journal of Organic Chemistry, 1989 , vol. 54, # 9 p. 2117 - 2125

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Citation Number: 22

Abstract

Allylpotassium derivatives were prepared from a variety of olefins by using Schlosser's base (BuLi/KOt-Bu). Reaction with (20S)-20-(iodomethyl) pregnane i-methyl ether (1) followed by deprotection gave in high yields a wide variety of and A24 (2a) sterols, including the naturally occurring desmosterol (37), fucosterol (33),