Total Syntheses of a class of complex quinone antitumor antibiotics, which includes naphthyridinomycin, saframycins A, C, renieramycins A-D, and mitomycins A, C, are proposed. These compounds have a similar quinone ring in common and are scarcely available from natural sources except for mitomycin C. Acyliminium ion cyclization, which we successfully used for the first total synthesis of saframycin B, will be used to construct the basic skeletons of naphthyridinomycin, saframycins A, D, and renieramycins A-D. Anodic oxidation will be used to form the unstable structure of mitomycins. Establishing efficient synthetic pathways to this class of compounds will help synthesizing their simpler analogues which might show more promising antitumor activities than their parent compounds.
