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化学学报
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化学学报 ›› 1981, Vol. 39 ›› Issue (4): 358-361. 上一篇    下一篇

研究简报

前列腺素中间体2-(6’-甲氧羰己基)环戊-2-烯-1-酮的合成

刘志煜, 韩卫平   

  1. 中国科学院上海有机化学研究所
  • 投稿日期:1979-04-04 发布日期:2013-06-03

THE SYNTHESIS OF A PROSTAGLANDIN INTERMEDIATE 2-(6’-METHOXYCARBONYLHEXYL)-CYCLOPENT-2-EN-1-ONE

LIU ZEI-Yu, HAN WEI-PING   

  1. Shanghai Institute of Organic Chemistry, Academia Sinica
  • Received:1979-04-04 Published:2013-06-03

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标题化合物(1)是合成11-去羟前列腺素E1(PGE1)及其衍生物的重要中间体[1].在引入羟基后所得化合物2是用1,4-加成法合成PGE1及其衍生物的关键中间体[2].因此最近几年文献中对合成1的研究仍有不少报道[3].我们曾从环戊酮合成1[2].现在本文报道另一种合成1的方法.

An alternative synthesis of the title compound (1) is reported. Reaction of ethyl: 8-(chloroformyl)-octanoate(4)with the Grignard reagent of 2-(2'-bromoethyl)-1, 3-diogane (3) gave compound 5. The latter was hydrolyzed in formic acid followed by alkaline cyclization and esterification to give compound 1 in 57% yield. Minor improvement in the preparation of compound 3 was also realized.