CONVERGENT TOTAL SYNTHESIS OF (+/-)-PROSTAGLANDIN-F2-ALPHA VIA CONJUGATE ADDITION AND REGIOSPECIFIC ENOLATE TRAPPING

被引：60

作者：

DAVIS, R ^{[1
]}

UNTCH, KG ^{[1
]}

机构：

[1] SYNTEX RES CORP,INST ORGAN CHEM,PALO ALTO,CA 94304

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 22期

关键词：

D O I：

10.1021/jo01336a004

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convergent total synthesis of (±-PGF2α via the conjugate addition of the dioctenylcuprate reagent 7a, derived from 1-iodo-3-hydroxyoct-1-cis-ene, to 4-[(tert-butyldimethylsilyl)oxy]cyclopent-2-en-l-one (2a) followed by regiospecific enolate trapping with ketene bis(methylthio)acetal monoxide (18) and stereospecific sulfenate-sulfoxide transformation is reported. The thioacetal intermediate 22, after stereospecific reduction and hydrolysis, is converted to the known ketol 24 and then to ±-PGF2α. © 1979, American Chemical Society. All rights reserved.

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页码：3755 / 3759

页数：5

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