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Original Articles

THE PREPARATION OF TWO NOVEL HOMOALLYLIC ALCOHOLS VIA THE REACTION OF EPOXIDE WITH PHOSPHONIUM YLIDE

Pages 269-275 | Received 14 Oct 2000, Accepted 20 Apr 2000, Published online: 27 Oct 2006
 

Abstract

Two novel homoallylic alcohols, E-4-(4-methoxyphenyl)- 1-phenyl-3-buten-1-01 and E-4-(3,4,5-trimethoxyphenyl)-1-phenyl-3-buten-1-01, were synthesised by the reaction of methelentriphenylphosphonium ylide with epoxide. The reaction first gave an initial betaine which upon treatment with butyl lithium gave a new ylide. When this new ylide reacted with the proper aldehyde, gave the corresponding homoallylic alcohol. Preliminary biological screening showed that the former alcohol possesses a significant estrogenic activity in rats. The latter alcohol was found to have partial antiestrogenic activity.

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