Chemistry of Antitumor Isoquinoline-quinone Alkaloids: Unexpected Oxidative Degradation of Saframycin S to Generate Simple Isoquinoline Alkaloids, Mimosamycin and Mimocin

Abstract

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.