谷斑皮蠹性信息素的立体选择性全合成  

Stereoselective synthesis of the sex pheromones of Trogoderma granarium

作　　者：杨天瑜 杨轩 高雪婷 符书铭 杜振亭 张涛 YANG Tian-yu;YANG Xuan;GAO Xue-ting;FU Shu-ming;DU Zhen-ting;ZHANG Tao(College of Chemistry and Pharmacy,Northwest A&F University,Yangling 712100,Shaanxi,China)

机构地区：[1]西北农林科技大学化学与药学院,陕西杨陵712100

出　　处：《农药》2023年第3期167-172,共6页Agrochemicals

基　　金：国家自然科学基金项目(No.31301712,No.32060627)。

摘　　要：[目的]为谷斑皮蠹性信息素的立体选择性合成提供新思路。[方法]采用(R)-2-甲基丁醇为手性原料,结合常见试剂1,3-丙二醇及1,8-辛二醇,主要通过Mitsnobu反应、Julia烯基化反应、戴斯-马丁氧化、Corey-Fush反应、端基炔与碘代烷烃耦联、Linlar Pd催化加氢等反应,合成谷斑皮蠹信息素(R,Z)-14-甲基十六碳-8-烯-1-醛。[结果]立体合成谷斑皮蠹信息素(R,Z)-14-甲基十六碳-8-烯-1-醛,反应总收率为3.3%[以(R)-2-甲基-1-丁醇计]。[Aims]A novel stereoselective synthesis method for the sex pheromone of Trogoderma granarium is develped.[Methods]Using(R)-2-methyl butanol as the chiral material,combined with 1,3-propanediol and1,8-octanediol,(R)-trogodermal,namely(R,Z)-14-methylhexadec-8-enal was synthesized through Mitsinobu reaction,Julia alkenylation reaction,Dess-Martin oxidation,Corey-Fush reaction,coupling of tenminal alkyne and haloalkane,Pd/C catalytic hydrogenation,etc.[Results]The total yield of this synthesis route is 3.3%according to the chial starting material.

关 键 词：(R Z)-14-甲基十六碳-8-烯-1-醛 性信息素 谷斑皮蠹 

分 类 号：TQ460.3[化学工程—制药化工]