Total Synthesis of the Antitumor Natural Product Polycarcin V and Evaluation of Its DNA Binding Profile

The convergent total synthesis of polycarcin V, a gilvocarcin-type natural product that shows significant cytotoxicity with selectivity for nonsmall-cell lung cancer, breast cancer, and melanoma cells, has been achieved in 13 steps from 7, 8, and 22; the sequence features a stereoselective alpha-C-glycosylation reaction for the union of protected carbohydrate 7' and naphthol 8. The association constant for the binding of polycarcin V to duplex DNA is similar to that previously reported for gilvocarcin V.