A divergent approach to synthesize C7 epoxyquinones from (-)-shikimic acid

A collective synthesis of the C7 epoxyquinones has been achieved by a concise and flexible strategy, in which the employment of (-)-shikimic acid as starting material permits the rapid preparation of the polyhydroxylated bromocyclohexene intermediate. (-)-Parasitenone, (+)-epoxydon and its monoactate, (-)-phyllostine and its acetate were readily synthesized via the oxirane ring closure of bromohydrin precursors. Moreover, the key intermediate was successfully extended for the synthesis of the epoxyquinones with a methyl group including (+)-epoformin, (+)-epiepoformin and (-)-theobroxide by sulfonate reduction method for the first time.