A NOVEL STEREOCONTROLLED SYNTHESIS OF (Z,Z)-3,13-OCTADECDIEN-1-YL ACETATE, THE SEX PHEROMONE OF SYNANTHEDON SPECIES
Starting from 10-undecenoic acid, a stereocontrolled synthesis of (Z,Z)-3,13-octadecadien-1-yl acetate with high sterochemical purity was achieved by the use of Wittig-olefinations for the introductions of (Z)-double bonds.
SYNTHESIS OF PHEROMONES, IV. CHEMISTRY OF THE WITTIG REACTION, I. EFFECTS OF REACTION CONDITIONS ON THE STEREOSELECTIVITY AND YIELD OF THE WITTIG REACTION
The reactions of nonstabilized triphenylphosphorus ylides with aldehydes have been studied in detail.The stereochemistry and yields of the alkene products are highly dependent upon base used for the generation of the ylide, the solvent and reaction temperature.The synthesis of sex pheromone components by Wittig reaction are also described.