Stereospecific synthesis of the sex pheromone of the passionvine mealybug, Planococcus minor

Abstract

A short and completely stereospecific synthesis of ( E)-2-isopropyl-5-methyl-2,4-hexadienyl acetate, the very recently identified sex pheromone of the passionvine mealybug Planococcus minor, is described. In the key step, CuI-catalyzed anti-addition of a Grignard reagent to a propargyllic alcohol intermediate gave the required trisubstituted alkene with 100% regio- and stereospecificity. The stereochemical purity of the pheromone is critically important because the ( Z)-isomer is a powerful behavioral antagonist.