A New Highly Stereospecific Synthesis of (E,Z)-2,13-Octadecadienyl Acetate, A Sex Pheromone Component of Some Lepidoptera Species

Abstract

The synthesis of the Z moiety of the title compound has been achieved by carbocupration of acetylene followed by alkylation with the appropriate organozinc reagent in the presence of catalytic pd°. The coupling of this intermediate with protected propargyl alcohol after adequate fonctionalisation affords the desired enyne in good yield. The stereoselective reduction of the triple bond followed by acetylation provides the pheromone in 99.8% stereoisomeric purity.