SYNTHESES OF OPTICALLY ACTIVE PHEROMONES WITH AN EPOXY RING, (+)-DISPARLURE AND BOTH THE ENANTIOMERS OF (3Z,6Z)-cis-9,10-EPOXY-3,6-HENEICOSADIENE

Article abstract of DOI:10.1016/S0040-4020(01)87314-2

(+)-Disparlure 1 and both the enantiomers of (3Z,6Z)-cis-9,10-epoxy-3,6-heneicosadiene 2 were synthesized in optically pure forms employing the Sharpless asymmetric epoxidation as the key-step.The natural pheromone 2 isolated from Estigmene acrea was shown to possess (9S,10R)-stereochemistry.