An Improved stereospecific synthesis of (Z,E)-tetradecadienal. Sex pheromone component of Stenoma cecropia

Abstract

(Z,E)-9, 11-Tetradecadienal, a sex pheromone component of Stenoma cecropia, has been synthesized in 7 steps and 61% overall yield. The synthesis utilized a palladium catalyzed coupling between 9-decynyl tert-butyldinethylsilyl ether and trans-1-iodo-butene, followed by reduction of triple bond of enyne with disiamylborane. Deprotection of silyl ether and oxidation afforded the desired aldehyde.