A NEW APPROACH TO CONJUGATED DIENES SYNTHESIS OF THE PHEROMONES OF LOBESIA BOTRANA AND BOMBYX MORI

Article abstract of DOI:10.1016/0040-4020(89)80066-3

Cis or trans epoxysilanes are regio and stereoselectively opened by Z-alkenyl cuprates, in the presence of BF₃*OEt₂, affording erythro or threo β-hydroxy silanes respectively.These are, in turn, transformed into E-Z conjugated dienes of high stereoisomeric purity by acidic or basic elimination.The method serves to synthetize the pheromones of Lobesia botrana and Bombyx mori.