Diastereoselective Synthesis of (8E,10z)-Tetradeca-8,10-dienal, the Sexual Pheromone of the Horse-Chestnut Leaf-Miner Cameraria Ohridella (lepidoptera: Gracillariidae)

Versatile classical and modern methods for a new synthesis of (8E,10Z)-tetradeca-8,10-dienal based on Sonogashira cross-coupling, Cahiez-Furstner reaction as well as other reactions using palladium, iron or copper as catalysts were described. We designed two ways employing two different strategies one of that involves an E-reduction and the other a Z- reduction with crucial importance in terms of diastereoselective synthesis. From the variously formulated pheromone baits, the one containing only the active isomer showed superior activity compared to the mixture of all isomers of 8,10-tetradecandienal. The synthesis of the pure E,Z diastereoisomer allowed to clarify their structure-bioactivity relationships to reveal the diversity in the stereochemical aspects of pheromone communications.