✦ LIBER ✦

Selective proton transfer of unsaturated esters : Syntheses of a trail-following pheromone for subterranean termites and megatomoic acid

✍ Scribed by Yoshihiko Ikeda; Junzo Ukai; Nobuo Ikeda; Hisashi Yamamoto

Publisher: Elsevier Science
Year: 1987
Tongue: French
Weight: 961 KB
Volume: 43
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)90008-0

No coin nor oath required. For personal study only.

✦ Synopsis

Deconjugative protonation of dienolates from (E)-2alkenoate using potassium disilazide as the base gives (z)-3alkenoate predominantly.

A trail-following pheromone for subterranean termites is synthesized stereoselectively with this method.

Deconjugative protonation of trienolates from (E,E)-2,4_tetradecedienoates gives (E,Z)-3,5-tetradecanoates which is hydrolyzed to give Megatomoic acid, a sex pheromone for a black carpet beetle Attagenus mesatoma.