Stereoselective Synthesis of Some Isomers of Dodecadien-1-ol: Compounds Related to the Pine Moth Sex Pheromone

Abstract

Four isomers of 5,7-dodecadien-l-ol were previously proposed as being the sex pheromone of the pine moth. The isomers were stereoselectively synthesized from 1-hexyne and tetrahydropyranyl ether of 5-hexyn-l-ol. The (5Z, 7Z)-isomer was synthesized by a Chodkiewic Cadiot reaction followed by hydroboration, and other three isomers by novel synthetic methods including the addition of zirconocene hydride [Schwarz’s reagent (C5H5)2Zn(H)Cl] to control the regioselective coupling reaction. The 5,8- and 5,9-dodecadien-l-ols were also synthesized by similar methods for comparison of their characteristics with the endogenous sex pheromone.