Regiospecific Quassinoidal A-Ring Synthesis via an Olefin Oxidation Strategy

Article abstract of DOI:10.1021/jo00246a036

A two-step method for oxidation of olefins to α-diketones is presented.Tricyclic olefin 12 was converted to three stereodefined 1,2-diols 14, 15, and 16.Swern oxidation of each of these substrates gave the same enolized α-diketone 17; base-catalyzed isomerization of this material quantitatively afforded an isomerized α-diketone 7B bearing the substitution pattern found in the antileukemia agent bruceantin (1A).The four α-diketones prepared are reasonably cytotoxic against P388 mouse leukemia.