Syntheses of Stereochemically Restricted Lactone-type Analogues of Jasmonic Acids

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.

• 7-epi-jasmonic acid
• jasmonic acid
• phytohormone
• jasmonic acid analogue