SYNTHESES AND NMR ANALYSES OF THE 8 GEOMETRIC ISOMERS OF 3,6,8-DODECATRIEN-1-OL, SUBTERRANEAN TERMITE TRAIL PHEROMONE

Eight geometric isomers of 3,6,8-dodecatrien-l-ol 1, the trail-following pheromone of subterranean termites (Reticulitermes sp. Banks), were synthesized via a Wittig olefination reaction. The conver-gent 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. © 1990.