油松毛虫性引诱剂(5Z,7E)-十二碳二烯醇及其乙酸酯和丙酸酯的合成

Synthesis of (5Z,7E)-Dodecadien-1-ol and Its Acetate and Propionate

从三甲基烯丙基硅烷和已炔出发,经过烷基化反应、硅卤消除反应、铝氢化反应以及烯基碘(4)和烯基铝(6)的偶联反应,实现了油松毛虫性引诱剂(1a—1c)的合成。总产率为20％,产物的立体化学纯度为94％。

Starting from allyltrimethylsilane and hexyne, (5Z, 7E)-dodecadien-1-ol was synthesized through alkylation, addition-elemination, hydroalumination and coupling reaction of vinyl iodide 4 with vinylalane 6. The total yield was 20% with stereoselectivity of 94%.