Conversion of 2,5-disubstituted furam into (Z)-jasmone

Abstract

Two new syntheses of (Z)-jasmone (3; R = (Z)-CH₂CH=CHCH₂Me) are reported. One is based on an initial oxidative opening of a 2,5- disubstituted furan (1; R = (Z)-CH₂CH₂CH=CHCH₂Me) to an enedione (2; R = (Z)-CH₂CH_2- CH=CHCH₂Me), the other on an efficient procedure for obtaining the keto acid (3; R = CH₂CO₂H) and the extension of the acetic acid side chain stereospecifically.