Identification, syntheses, and characterization of the geometric isomers of 9,11-hexadecadienal from female pheromone glands of the sugar cane borer Diatraea saccharalis.

Chemical analysis of the pheromone glands of the sugar cane borer Diatraea saccharalis has shown the presence of the four geometric isomers of 9,11-hexadecadienal (1-4), in addition to hexadecanal and (Z)-hexadec-11-enal. We here report the syntheses and characterization of compounds 1-4. One starting material, 9-decen-1-ol, has been used to obtain all of them via divergent synthetic routes.