若干鳞翅目昆虫性信息素——Z/E-9-烯脂肪醇醋酸酯的合成

Syntheses of Z / E-9-Alkenol Acetates-Some Lepidoptera Insect Sex Pheromones

本文提出了合成若干鳞翅目昆虫性信息素—Z/E-9-烯脂肪醇醋酸酯的新方法．即从易得的天然不饱和脂肪酸—10-十一碳烯酸出发,经臭氧化硼氢化钠还原合成相应的10-羟基癸酸,随后经乙酰化得10-乙酰氧基癸酸,再经溴代脱羧反应合成了关键中间体9-乙酰氧基溴代壬烷,最后经维悌希反应合成了目标物．其中,Z/E-9-烯十二碳醇醋酸脂为甘蔗黄螟和枣粘虫等昆虫的性信息素;Z/E-9-烯十四碳醇醋酸酯为茶小卷叶蛾和桔卷叶蛾等昆虫的性信息素;Z/E-9-烯十六碳醇醋酸酯为稻螟蛉的性信息素;Z/E-9-烯十三碳醇醋酸酯和Z/E-9-烯十五碳醇醋酸酯为类似物．

This paper present a new method of syntheszing Lepidoptera Insect Sex Pheromones -Z / E-9-Alkenol Acetates, the new synthetic route is based on unsaturat-ed aliphatic acid, 10-undecenoic acid, via ozonization, sodium borhydride (Pot-assiumborhydride)reduction of their ozonides, acetylation, halogenative decarboxylation and Wittig reaction. We have syntsesized five insect Sex Pheromones (5a-e). they are Argyroloce schistacena(5e), Adoxophyes orana(5c)、Rice green caterpilliar(5e), (5b) and (5d) are their analogues.The synthetic method has adventages of starting material available easily, inexpensive and short route etc, The structures of compounds(5a-e)and their intermediates have been comfirmed by IR and 1HNMR spectra.