Chemistry of antitumor isoquinolinequinone alkaloids: unexpected oxidative degradation of saframycin s to generate simple isoquinoline alkaloids, mimosamycin and mimocin

摘要

Saframycin S, prepared by treating saframycin A with silver nitrate in aqueous acetonitrile, was transformed into simple isoquinolinequinones, mimosamycin and mimocin, by treatment with a catalytic amount of trifluoroacetic acid (TFA) in chloroform. The proposed mechanism for this oxidative degradation is presented.