SYNTHESIS OF KETOLS OF NATURAL PYRETHRINS

被引:77
作者
CROMBIE, L
HEMESLEY, P
PATTENDEN, G
机构
[1] Department of Chemistry, University College (University of Wales), Cardiff, Cathays Park
来源
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC | 1969年 / 06期
关键词
D O I
10.1039/j39690001016
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A stereospecific five-stage synthesis of (±)-cis-pyrethrolone is described, involving cis-octa-1,3-dien-7-one as the key intermediate. The ethylene acetal of this ketone was made by a Wittig reaction, under 'salt-free' condiditions, with vaporised acraldehyde. The overall yield for the synthesis was 21%. and it provides highly pure (±)-cis-pyrethrolone for the first time. The material is spectrally identical with a sample of natural (+)-pyrethrolone. Improved syntheses of both (±)-cis-cinerolone and (±)-cis-jasmololone are reported. The cis-side chains are introduced by Wittig reactions or by selective hydrogenation of acetylenic intermediates. An allenic formulation, entertained for natural pyrethrolone in the early literature, is synthesised.
引用
收藏
页码:1016 / +
页数:1
相关论文
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