DDQ-Catalyzed Oxidative C(sp3)–H Functionalization of Aryltetralins and Subsequent Chemoselective Oxidative Demethylation to Access Dihydronaphthalenes and Dihydronaphthoquinones

A highly controlled DDQ-catalyzed oxidative C(sp3)-H functionalization of three contiguous carbon atoms in aryltetralins is reported for efficient access to diverse oxygenated dihydronaphthalene scaffolds. The first total synthesis of pachypostaudin B is realized. Further, a CAN-mediated chemoselective oxidative demethylation on the dihydronaphthalene scaffolds is demonstrated to arrive at the rarely observed dihydronaphthoquinone core in moderate to good yields. The present methodology enables quick access to a library of magnoshinin and merrilliaquinone analogs.