Regioselective cycloadditions between the cyclohexadienones and the ortho-quinone dimethide, which is thermally generated from the corresponding 1, 3-dihydro-1-methoxy-2, 2- dioxide benzo [c] thiophene, are reported. The synthetic sequence provides rapid access to highly substituted anthracyclic system and may be of use for construction of the natural product (+)-rishirilide B.