Insect pheromones and their analogs III. Synthesis of the sex attractants of some Lepidoptera

Abstract

A new route to the synthesis of a number of attractants of Lepidoptera (Argyrotaenia velutinana, Mamestra configurata, and Lycorea ceres ceres) have been developed. These substances are acetates of enols with the cis configuration: tetradec-11-en-1-ol, hexadec-11-en-1-ol, and octadec-11-en-1-ol, respectively. The constants of the substances obtained agree completely with those given in the literature. The method is based on the coupling of the C3, C5, and C7 aldehydes with methyl 11-bromoundecanoate (I) by the Wittig reaction. To obtain compound (I) from methyl undeca-2E,5E,10-trienoate or methyl undeca-10-enoate we used hydroboration according to Brown followed by hydrogenation and bromination of the alcohol obtained. The advantage of this method is the use as starting materials of esters of unsaturated acids readily obtained by the homogeneous catalytic co-oligomerization of 1,3-dienes with acrylates. © 1980 Plenum Publishing Corporation.