Total syntheses of a class of complex quinone antitumor antibiotics, which include naphthyridinomycin, saframycin A and C, renieramycin A, B, C, and D, and mitomycin A and C, are proposed. These compounds have a similar quinone ring in common and are scarcely available from natural sources except for mitomycin C, a clinically used antitumor agent. In addition, a total synthesis of quinocarcin with close structural resemblance to naphthyridinomycin is proposed. A vast number of experimental results obtained from the synthetic studies of naphthyridinomycin, safframycin A and B will be used for the synthesis of saframycin C, renieramycins, and quinocarcin. For the synthesis of mitomycins we plan to synthesize AX-2, a recently isolated congener of mitomycin A which has been shown to isomerize readily to mitomycin A. The advantage of this approach is that there is no danger of aromatization, the problem which has hampered numerous synthetic attempts in the past. Establishing efficient synthetic pathways to this class of compounds will help synthesizing their analogues which might exhibit more promising antitumor activities than their parent compounds.
