Tetrahedron p. 2695 - 2706 (1990)
Update date:2022-09-26
Topics:
Eya, Bryan K.
Otsuka, Toshikazu
Kubo, Isao
Wood, David L.
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.
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(1938)
