Stereospecific synthesis of (Z,Z)-3,5-tetradecadienoic acid, a component ofAttagenus elongatulus (Casey) pheromone.

A simple stereospecific synthesis of (Z,Z)-3,5-tetradecadienoic acid is described based upon coupling of 1-decyne and 3-butyn-1-ol to give 3,5-tetradecadiyn-1-ol. Subsequent reduction of the diyne to (Z,Z)-3,5-tetradecadien-1-ol and oxidation of the dienol gave the desired acid.Attagenus elongatulus were strongly attracted to the pure acid.