Abstract: Stereochemical control of the Wittig reaction of the primary aldehyde 6 with the nonstabilized alkylide, triphenylphosphonium n-pentylide 7, is achieved by controlled partial equilibration of the intermediate adducts. These conditions are applied to the direct synthesis of the mixture of insect sex pheromones," gossyplure", which is a 1! 1 mixture of (72, llZ)-and (7Z, llE)-7, ll-hexadecadien-l-yl acetate (la and 2a, respectively). The ...
