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Paper | Regular issue | Vol 55, No. 3, 2001, pp.545-555
Published online, 1st January, 1970
DOI: 10.3987/COM-00-9138
A Singlet Oxygen Mediated New Access to Hydroxyindolenine-Catharanthine Derivatives by Two Sequential Oxidations

Clotilde Ferroud* and Patrice Rool

*Laboratoire de Chimie Organique associe au CNRS, Conservatoire Naitonal des Arts et Metiers, 292, rue Saint Martin, 75141 Paris Cedex 03, France


Formation of hydroxyindolenine derivatives by photoinduced oxidation by singlet oxygen of intermediate 3β-cyanocatharanthine (3) allows us to synthesize under mild conditions new alkaloids derivatives, 3β-cyano-7β-hydroxyindolenine-catharanthine (5), 3β-cyano-7β-hydroxyindolinecatharanthine (6) and 7β-hydroxy-indolenine-catharanthine (7), bearing protected indole moities.