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

[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.