SYNTHETIC MODIFICATIONS OF WITHANOLIDES WITH AN ALPHA-ORIENTATED SIDE-CHAIN

被引：11

作者：

GLOTTER, E

KUMAR, S

SAHAI, M

GOLDMAN, A

KIRSON, I

MENDELOVICI, M

机构：

[1] Faculty of Agriculture, Hebrew University of Jerusalem

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 04期

关键词：

D O I：

10.1039/p19910000739

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In view of the antitumour activity of withanolide E [(20S,22R)-5-beta,6-beta-epoxy-14-alpha,17-beta,20-trihydroxy-1-oxowitha-2,24-dienolide] and 4-beta-hydroxywithanolide E, synthetically modified analogues were prepared. In these compounds, the alpha-orientation of the side-chain was retained. Its degree of bending with respect to the carbocyclic skeleton depends on the presence or absence of the 14-alpha-OH group. Elimination of this group leads to the formation of the 14,20-oxido-bridged and DELTA-14-compounds. Epoxidation of the latter afforded 14-alpha,15-alpha-epoxides. With the exception of several 5,6-chlorohydrins, most compounds possess an epoxide ring, allylic or homoallylic with respect to the ring A enone.

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页码：739 / 745

页数：7

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