桃小食心虫性信息素——(Z)-7-二十碳烯-11-酮的简便合成

Simple Synthesis of(Z)-7-Eicosen-11-one—the Sex Pheromone of Peach Fruit Moth

桃小食心虫是危害最大的果树害虫之一,其性信息素主要成分为(Z)-7-二十碳烯-11-酮.从2,3-二氢呋喃出发,经酸水解得到4-羟基丁醛,与正庚基三苯基溴化磷制备的Wittig试剂反应得到(Z)-4-十一碳烯-1-醇,经氧化得到(Z)-4-十一碳烯醛,再经格氏加成得到(Z)-7-二十碳烯-11-醇,氧化后得到目标产物.

Peach fruit moth is one of the most serious pests, whose sex pheromone is （Z）-7-eicosen- 11-one. Synthesis of the compound was achieved from 2,3-dihydrofuran. Firstly, acidic hydrolysis of 2,3-dihydrofuran gave 4-hydroxybutanal, which reacted with the ylide prepared from heptyltriphenylphosphonium bromide to afford （Z）-4-undecen-l-ol. The alcohol was oxidated followed by Grignard addition and further oxidation to give the target product.