19926-64-8Relevant articles and documents
Selective Proton Transfer of Unsaturated Esters. Syntheses of A Trail-Following Pheromone for Subterranean Termites and Megatomoic Acid
Ikeda, Yoshihiko,Ukai, Junzo,Ikeda, Nobuo,Yamamoto, Hisashi
, p. 743 - 754 (1987)
Deconjugative protonation of dienolates from (E)-2-alkenoate using potassium disilazide as the base gives (Z)-3-alkenoate predominantly.A trail-following pheromone for subterranean termites is synthesized stereoselectively with this method.Deconjugative protonation of trienolates from (E,E)-2,4-tetradecadienoates gives (E,Z)-3,5-tetradecanoates which is hydrolyzed to give Megatomoic acid, a sex pheromone for a black carpet beetle Attagenus megatoma.
Syntheses and NMR analyses of the eight geometric isomers of 3,6,8-dodecatrien-1-ol, subterranean termite trail pheromone
Eya, Bryan K.,Otsuka, Toshikazu,Kubo, Isao,Wood, David L.
, p. 2695 - 2706 (2007/10/02)
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.