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Free keywords:
conjugated dienals; stereoselective synthesis; Negishi reaction; sex pheromones; Cameraria ohridella; cross-coupling reactions; alkenes;
dienes;
Abstract:
(8E,10Z)-Tetradeca-8,10-dienal (1a), sex pheromone of the horse chestnut leaf miner (Cameraria ohridella; Lepidoptera, Gracillariidae), and its geometrical isomers (1b-1d) were efficiently synthesized using tetrakis(triphenylphosphine)palladium catalyzed cross-coupling reactions of alk-1-ynes or alkenyl alanes with corresponding vinyl iodides. The stereoisomeric purity of obtained tetradecadienals 1a-1d was higher than 95% (GC). Relative electroantennographic (EAG) activities of the prepared compounds la-ld elicited on male antennae supported the previously published identification of the C. ohridella sex pheromone.
