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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

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Hoskovec, M., Šaman, D., & Svatoš, A. (2000). Synthesis of (8E,10Z)-tetradeca-8,10-dienal, sex pheromone of horse chestnut leafminer (Cameraria ohridella), and all its geometrical isomers. Collection of Czechoslovak Chemical Communications, 65(4), 511-523. doi:10.1135/cccc20000511.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0015-10EF-7
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.