Total Synthesis of (±)-Plumbazeylanone

Abstract

The first total synthesis of plumbazeylanone (1), which is a trimer of naphthoquinone, was carried out successfully utilizing the unsymmetrical methylene-bridged dimer with the naphthoquinone unit and the naphthol unit, 11b as a key intermediate in 11 steps. This synthesis features a regioselective nucleophilic 1, 2-addition reaction and dinone-phenol-type rearrangement.