Syntheses and NMR analyses of the eight geometric isomers of 3,6,8-dodecatrien-1-ol, subterranean termite trail pheromone

Article abstract of DOI:10.1016/S0040-4020(01)88364-2

Eight geometric isomers of 3,6,8-dodecatrien-1-ol 1, the trail-following pheromone of subterranean termites (Reticulitermes sp. Banks), were synthesized via a Wittig olefination reaction. The convergent syntheses of 1 consisted of a combination of two fragments, each containing an olefin with a fixed configuration, by formation of a third double bond to give a mixture of two geometric isomers. The mixtures of 1 were resolved by recycle high-performance liquid chromatography methods. ¹H and ¹³C NMR peak assignments of the individual isomers were accomplished by homonuclear COSY, and one-bond CH correlation spectroscopy.