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Syntheses of stereochemically restricted lactone-type analogues of jasmonic acids
H Toshima1, H Aramaki, A Ichihara
1Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Sapporo, Japan. toshima@chem.agr.hokudai.ac.jp
Bioscience, Biotechnology, and Biochemistry
|October 31, 2000
Abstract:
5-Oxa-7-epi-jasmonic acid and 5-oxa-jasmonic acid, which are stereochemically restricted lactone-type analogues of jasmonic acids, were synthesized via three-component coupling of 2(5H)-furanone, tert-butyl acetate and 1-bromo-2-pentyne. After acidic deprotection of the tert-butyl esters, the (Z)-olefin was introduced by catalytic partial reduction with the Lindlar catalyst to give the desired analogues.