A versatile and convenient protocol for the stereocontrolled synthesis of olefinic insect pheromones

Article abstract of DOI:10.1016/0968-0896(96)00016-8

A combination of the Horner-Emmons synthesis of alkyl 2,4-dienoates with their hydrogenation over complex L·Cr(CO)₃ catalysts (L = 3CO or arene) provides a versatile, stereocontrolled and operationally simple approach to the (Z)-disubstituted, (Z)-trisubstituted, (E)-trisubstituted alkenes and skipped (Z,Z)-disubstituted diolefins with a homoallylic type of function. This protocol, sometimes supplemented by an enzymatic hydrolysis, was successfully applied to the synthesis of configurationally pure (gp ≥ 98%) pheromones of the furniture carpet beetle, dry bean beetle, rusty grain beetle, square-necked grain beetle and of a trail-following pheromone mimic for subterranean termites