Chemoenzymatic Access to Versatile Epoxyquinol Synthons

The enantiomerically pure and readily available metabolites 10−12 have been converted over four simple steps into the epoxyquinol derivatives 22−24, respectively. Compounds 23 and 24 or their immediate precursors have been exploited in efficient total syntheses of (−)-bromoxone (ent-1), (−)-epiepoformin (ent-2), (−)-harveynone (4), (+)-panepophenanthrin (6), and (+)-hexacyclinol (9).