New Synthetic Technology for the Construction of N-Containing Quinones and Derivatives Thereof: Total Synthesis of Epoxyquinomycin B

A mechanistically inspired tandom Dess–Martin periodinane (DMP) induced oxidation sequence converts anilides into N-substituted p-quinones or o-azaquinones depending on the aromatic nucleus substitution. The application of this technology resulted in an expedient total synthesis of the potent anti-arthritic agent epoxyquinomycin B (see picture).