| Title: | A versatile and convenient protocol for the stereocontrolled synthesis of olefinic insect pheromones |
| Author(s): | Vasil'ev AA; Vlasyuk AL; Gamalevich GD; Serebryakov EP; |
| Address: | "N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation" |
| DOI: | 10.1016/0968-0896(96)00016-8 |
| ISSN/ISBN: | 0968-0896 (Print) 0968-0896 (Linking) |
| Abstract: | "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 functionally. This protocol, sometimes supplemented by an enzymatic hydrolysis, was successfully applied to the synthesis of configurationally pure (gp > or = 98%) pheromones of the furniture carpet beetle, dry bean beetle, rusty grain beetle, square-necked grain beetle and a trail-following pheromone mimic for subterranean termites" |
| Keywords: | "Alkenes/*chemical synthesis Animals Chromatography, Gas Coleoptera/*chemistry Insecta/*chemistry Magnetic Resonance Spectroscopy Molecular Conformation Pheromones/*chemical synthesis;" |
| Notes: | "MedlineVasil'ev, A A Vlasyuk, A L Gamalevich, G D Serebryakov, E P eng Research Support, Non-U.S. Gov't England 1996/03/01 Bioorg Med Chem. 1996 Mar; 4(3):389-400. doi: 10.1016/0968-0896(96)00016-8" |
