Collect. Czech. Chem. Commun. 2000, 65, 511-523

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

Michal Hoskovec, David Šaman and Aleš Svatoš*

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic


(8E,10Z)-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.

Keywords: Conjugated dienals; Stereoselective synthesis; Negishi reaction; Sex pheromones; Cameraria ohridella; Cross-coupling reactions; Alkenes; Dienes.

References: 18 live references.