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Communication | Special issue | Vol 61, No. 1, 2003, pp.79-86
Published online, 7th August, 2003
DOI: 10.3987/COM-03-S45
Chemistry of Antitumor Isoquinolinequinone Alkaloids: Unexpected Oxidative Degradation of Saframycin S to Generate Simple Isoquinoline Alkaloids, Mimosamycin and Mimocin

Naoki Saito,* Yu-ichi Koizumi, Chieko Tanaka, Khanit Suwanborirux, Surattana Amnuoypol, and Akinori Kubo*

*Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan

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.