Total Synthesis of Pradimicinone, the Common Aglycon of the Pradimicin–Benanomicin Antibiotics

A benzo[a]naphthacenequinone core, an amino acid, and a disaccharide are the constituents of pradimicin–benanomicin antibiotics 1 (R1=disaccharide), a class of natural products with significant antifungal and anti-HIV activities. The first total synthesis of pradimicinone (benanomicinone, 1; R1=H), the common aglycon of this class of natural products, has now been achieved based on the transmission of chirality during the pinacol cyclization of 2,2′-biaryldicarbaldehydes.