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Note | Regular issue | Vol 53, No. 10, 2000, pp.2241-2246
Published online, 1st January, 1970
DOI: 10.3987/COM-00-8990
■ A Synthesis of (±)-Dihydronitraraine

Emmi Päiviö, Mathias Berner, Arto Tolvanen, and Reija Jokela*

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

Abstract

A short synthesis of (±)-dihydronitraraine (1) from an unknown 5,6,7,8-tetrahydroisoquinoline ester (3) is presented. The Fry reaction of tetrahydroisoquinolinium salt (4), followed by cyclization and hydrogenation, gave an alloyohimbane derivative (6), which was reduced to yield dihydronitraraine (1). Complete 1H NMR and 13C NMR data of dihydronitraraine (1) and intermediate (6) are reported.