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Paper | Regular issue | Vol 36, No. 12, 1993, pp.2707-2721
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6481
Synthesis of Potential Cytotoxic Quaternary Ammoniums by Oxidation of Eburnane Alkaloids

Guy Lewin,* Corinne Schaeffer, Alain Pierré, Nicolas Guilbaud, Ghanem Atassi, and Jacques Poisson

*Laboratoire de Pharmacognosie, Faculté de Pharmacie, 1, rue Vaubénard, 14032 Caen Cedex, France

Abstract

Oxidation of vincamine and substituted analogs on ring-A was carried out in two steps: benzylic oxidation by Jones reagent and aromatization of ring-C with Hg(OAc)2 or Tl(OCOCF3)3 in trifluoroacetic acid. Final compounds are quaternary ammoniums which exhibited weak cytotoxicity or no cytotoxicity according to substituents on ring-A and nature of ring-E.