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Synthesis of (8E,10Z)-Tetradeca-8,10-dienal, Sex Pheromone of Horse Chestnut Leafminer (Cameraria ohridella), and All Its Geometrical Isomers

2000; Wiley-VCH; Volume: 65; Issue: 4 Linguagem: Inglês

10.1135/cccc20000511

1212-6950

Michal Hoskovec, David Šaman, Aleš Svatoš,

Research on scale insects

(8 E ,10 Z )-Tetradeca-8,10-dienal ( 1a ), sex pheromone of the horse chestnut leafminer ( 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 1a - 1d elicited on male antennae supported the previously published identification of the C. ohridella sex pheromone.