Total synthesis of (+/-)-methyl rishirilide B

formula: see text] A regio- and stereospecific total synthesis of (+/-)-methyl rishirilide B (2b), and (alpha)2-macroglobulin inhibitor, is described. A key feature of the synthetic plan was regiospecific construction of a hydroanthracenone intermediate through condensation of a phenylsulfonyl isobenzofuranone with a functionalized 2-cyclohexen-1-one. Introduction of the vicinal trans-hydroxyl groups in the densely functionalized A-ring was accomplished via a novel one-pot procedure that involved oxidation of enolate anions with the Davis reagent.