Short-route synthesis of (3E,5Z)-tetradecadienoic acid (megatomic acid), the sex attractant of the black carpet beetle

Authors
Yadav, JS Reddy, EJ Ramalingam, T
Citation
Js. Yadav et al., Short-route synthesis of (3E,5Z)-tetradecadienoic acid (megatomic acid), the sex attractant of the black carpet beetle, NEW J CHEM, 25(2), 2001, pp. 223-225
Citations number
19
Categorie Soggetti
Chemistry
Journal title
NEW JOURNAL OF CHEMISTRY
ISSN journal
11440546 → ACNP
Volume
25
Issue
2
Year of publication
2001
Pages
223 - 225
Database
ISI
SICI code
1144-0546(2001)25:2<223:SSO(A(>2.0.ZU;2-1
Abstract
A new and expeditious route to (3E,5Z)-3,5-tetradecadienoic acid (megatomic acid), the sex attractant of the black carpet beetle Attagenus megatoma (F abricius), is reported which proceeds with 97% stereoselectivity; Cadiot-Ch odkiewicz cross-coupling of 1-decyne and 4-bromo-3-butyn-1-ol in the presen ce of CuCl, followed by stereoselective reductions and Jones oxidation, giv es the target molecule, with the synthetic pheromone showing a positive ele ctrophysiological response.