Journal
NEW JOURNAL OF CHEMISTRY
Volume 25, Issue 2, Pages 223-225Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b007956l
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A new and expeditious route to (3E,5Z)-3,5-tetradecadienoic acid (megatomic acid), the sex attractant of the black carpet beetle Attagenus megatoma (Fabricius), is reported which proceeds with 97% stereoselectivity; Cadiot-Chodkiewicz cross-coupling of 1-decyne and 4-bromo-3-butyn-1-ol in the presence of CuCl, followed by stereoselective reductions and Jones oxidation, gives the target molecule, with the synthetic pheromone showing a positive electrophysiological response.
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