18829-88-4Relevant academic research and scientific papers
A versatile and convenient protocol for the stereocontrolled synthesis of olefinic insect pheromones
Vasil'ev, Andrei A.,Vlasyuk, Alexei L.,Gamalevich, Galina D.,Serebryakov, Edward P.
, p. 389 - 400 (1996)
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
