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■ Tryptophan Derived Pyridinium Salts: Preparation, Reductive Cyanation and Addition Reactions

Ari Koskinen and Mauri Lounasmaa*

*Laboratory of Organic Chemistry, Helsinki University of Technology, P.O. Box 6100,FIN-02015 HUT, Espoo, Finland

Abstract

Tryptophan derived pyridinium salts 8 can be prepared from methyl 2-tosyloxy-3-(3-indolyl)propionate 6d. The salt formation was usually accompanied by rearrangement in the indole side chain. Behaviour of the pyridinium salts under reductive cyanation conditions and in nucleophilic addition reactions were studied.