Synthesis of (22R,23R,24S)-24-methyl-5α-cholestane-3β,6α,22,23-tetraol, a biosynthetic precursor of brassinolide

被引：2

作者：

Khripach, VA ^{[1
]}

Zhabinskii, VN ^{[1
]}

Pavlovskii, ND ^{[1
]}

机构：

[1] Natl Acad Sci Belarus, Inst Bioorgan Chem, Minsk 220141, BELARUS

来源：

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 37卷 / 11期

关键词：

D O I：

10.1023/A:1013804119279

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A biosynthetic precursor of brassinolide, (22R,23R,24S)-24-methyl-3alpha-cholestane-3beta,6alpha,22,23-tetraol was synthesized from Delta(23)-22-keto steroid which was obtained from the corresponding 20-carbonitrile oxide. The side chain was built up by a series of successive transformations: hydride reduction of the initial enone, epoxidation of the allyl-like alcohol, and copper(I) cyanide-catalyzed opening of the 23,24-epoxy ring. The cyclic fragment was completed by opening of the cyclopropane ring with subsequent hydroboration and oxidation of the Delta(5)-bond.

引用

页码：1570 / 1574

页数：5

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