A STEREOSELECTIVE SYNTHESIS OF (Z,E)-9,11-TETRADECADIENYL-1-ACETATE, A MAJOR COMPONENT OF THE SEX PHEROMONE OF SPODOPTERA LITURA

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Abstract
Wittig reaction of 9-acetoxynonyl-triphenylphosphonium bromide (7) with (E)-2-pentenal (8) gave stereoselectively (85–90%) (Z,E)-9,11-tetradecadienyl-1-acetate (1) together with a small amount of the (E,E)-isomer (6) which was removed from the mixture by the formation of the Diels-Alder adduct (13) with tetracyanoethylene. In contrast, Wittig reaction of (E)-2-pentenyl-triphenylphosphonium bromide (3) with 9-acetoxynonyl aldehyde (5) afforded a mixture of 1 and 6.