An alternative synthesis of (8E,10Z)-tetradeca-8,10-dienal, sex pheromone of horse-chestnut leafminer (Cameraria ohridella)

The stereoselective synthesis of the sex pheromone of horse-chestnut leafminer was efficiently carried out using methodology based on the Pd(0)-catalyzed cross-coupling of 1-pentynylmagnesium bromide with the corresponding vinyl iodides as the key step.

Synthesis of sex pheromone of horse-chestnut leafminer (1) has been achieved by the palladium-catalyzed cross-coupling reaction of 1-pentynylmagnesium bromide and suitable vinyl iodides as the key step to construct the conjugated diene moiety of the title compound.