STEREOCHEMICAL COURSE OF THE CHEMICAL AND CATALYTIC REDUCTION OF 11-OXO-5-ALPHA,14-BETA-CHOLEST-8-EN-3-BETA-OL - SYNTHESIS OF 8-ALPHA,9-ALPHA,14-BETA-STEROIDS,8-ALPHA,9-BETA,14-BETA-STEROIDS, AND 8-BETA,9-ALPHA,14-BETA-STEROIDS

被引：7

作者：

PATTERSON, DG ^{[1
]}

DJERASSI, C ^{[1
]}

机构：

[1] STANFORD UNIV,DEPT CHEM,STANFORD,CA 94305

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 11期

关键词：

D O I：

10.1021/jo01325a027

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The lithium-ammonia overreduction of ll-oxo-5α,14β-cholest-8-en-3β-ol (1) was shown to give equal amounts of 5α,8α,9a, 14β-cholestane-3β,llβ-diol (2) and 5α,8β,9α,14β-cholestane-3β,lla-diol (3) by conversion of the diols to hydrocarbons of known stereochemistry. In contrast to 14α- and 14β-steroidal 11-ketosapogenins (which are stable to base), the 5α,8α,9α, 14β-11-ones in the present study provided through base equilibration a route to the unknown 8α,9β,14β stereochemistry. The CD spectra of the ll-keto-5α, 8α,9α,14β-, and -5α,8β, 39α, 14β-, and -50, 8α,9β,14β-steroids provide evidence for nonchair conformations in rings B and/or C of the steroid skeleton. © 1979, American Chemical Society. All rights reserved.

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页码：1866 / 1871

页数：6

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