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Review | Regular issue | Vol 48, No. 6, 1998, pp.1275-1290
Published online, 1st January, 1970
DOI: 10.3987/REV-98-497
Acid-catalysed C-3 Epimerization of Reserpine and Other Indolo-[2,3-a]quinolizidines

Mauri Lounasmaa,* Mathias Berner, and Arto Tolvanen

*Laboratory for Organic and Bioorganic Chemistry, Technical University of Helsinki, P.O. Box 6100, FIN-02150 HUT Espoo, Finland


The acid-catalysed C-3 epimerization of the indole alkaloid reserpine (1) and other closely related indolo[2,3-a]quinolizidines is reviewed. The three mechanisms that have been proposed and relevant experimental findings are discussed. Representative examples of C-3 epimerization reactions are included.