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Report | Regular issue | Vol 23, No. 7, 1985, pp.1735-1740
Published online, 1st January, 1970
DOI: 10.3987/R-1985-07-1735
■ Synthesis of the Ixoquinuclidine Ring System

Mauri Lounasmaa,* Tarja Tamminen, and Reija Jokela

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

Abstract

The formation of the biochemically important isoquinuclidine ring system by intramolecular condensation of an appropriately substituted piperidine-5-carbaldehyde derivative 6 is described. The direct acylation of the intermediate α-aminonitrile 5a (prepared by the modified Polonovski reaction) to the piperidine-5-carbaldehyde derivative 6 could be achieved only in low yield. However, if the α-aminonitrile 5a was transformed, before the acylation, to the “dimer” 7 of tetrahydroanabasine type, the piperidine-5-carbaldehyde derivative 6 could be obtained in much higher total yield.