Syntheses of unconjugated (Z,Z)-diolefinic insect pheromones on insoluble polymer supports

Abstract

A 2% cross-linked styrene-divinylbenzene copolymer containing pendant trityl chloride groups was used as the solid support in the synthesis of (Z, Z)-3,13-octadecadien-1-yl acetate, a component of the sex attractant of the lesser peachtree borer,Synanthedon pictipes, the peachtree borer,Synanthedon exitiosa, and the cherry tree borer,Synanthedon hector. This solid-phase synthesis is compared with a similar synthetic approach in solution. The solid-phase synthesis of (Z, Z)-7,11-hexadecadien-1-yl acetate, a component of the pheromone of the pink bollworm moth,Pectinophora gossypiella is described.