SYNTHESIS OF WASABIDIENONE-A VIA A NOVEL ACYL REARRANGEMENT REACTION FROM CARBON TO OXYGEN

Wasabidienone A (WA), a tautomeric mixture of [(2R)-2-methylbutyryloxy ]-cyclohexa-2,4-dien-1-one (1a) and -[(2R)-2-methylbutyryloxy]cyclohex a-2,4-dien-1-one (1b) was synthesized via a novel rearrangement reacti on of an acyl group from carbon to the beta-hydroxy oxygen on the cycl ohexadienone ring. This reaction may occur during fermentation of Phom a wasabiae to form WA from WB1.