Bioscience, Biotechnology, and Biochemistry 2000-09-01

Syntheses of stereochemically restricted lactone-type analogues of jasmonic acids.

H Toshima, H Aramaki, A Ichihara

Index: Biosci. Biotechnol. Biochem. 64(9) , 1988-92, (2000)

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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.