SHORT-STEP STEREOSELECTIVE SYNTHESIS OF 2-ALPHA,3-ALPHA,22-TRIACETOXY-23,24-DINOR-5-ALPHA-CHOLAN-6-ONE - KEY INTERMEDIATE FOR THE PREPARATION OF 24(1)-NORBRASSINOLIDE, DOLICHOLIDE AND DOLICHOSTERONE

被引：22

作者：

HAZRA, BG

PORE, VS

JOSHI, PL

机构：

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 15期

关键词：

D O I：

10.1039/p19930001819

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereoselective synthesis of 6-oxo-23,24-dinor-5alpha-cholan-2alpha,3alpha,22-triyl triacetate 9 was achieved in 44% overall yield in nine steps starting from 3beta-hydroxyandrost-5-en-17-one 8. The important features of this synthesis are the modified Wittig reaction on the 17-oxo steroid 8 and the stereospecific generation of the chiral centre at C-20 by a resin-catalysed ene reaction on (Z)-3beta, p-tolylsulfonyloxypregna-5,17(20)-diene 11.

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页码：1819 / 1822

页数：4

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