An efficient and stereoselective synthesis of insect pheromones by way of nickel-catalyzed Grignard reactions. Syntheses of gossyplure and pheromones of Eudia pavonia and Droxophila melanogaster

Article abstract of DOI:10.1016/S0040-4020(01)88230-2

Three pheromones, (6Z,11Z)-hexadeca-6,11-dien-1-yl acetate (from Eudia pavonia), (5Z,9Z)-heptacosa-5,9-diene (from Drosophila melanogaster) and gossyplure, have been synthesized each by two consecutive consequences of nickel-assisted Grignard reactions with cyclic enol ethers and preparation of Grignard reagents from the resultant alcohols.