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Paper | Regular issue | Vol 34, No. 1, 1992, pp.37-49
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5810
Intramolecular Cyclization of Allylsilyl Substituted N-Acyliminium Ions. Access to 1- and 2-Azabicyclo[X.Y.0]alkanes. Total Synthesis of (±)-Mesembrine

Yvonne Gelas-Mialhe, Jean-Claude Gramain, Hassane Hajouji, and Roland Remuson*

*Laboratoire de Chimie des Substances Naturelles, URA CNRS 485, Université Blaise Pascal (Clemont-II), 63177 Aubière Cedex, France

Abstract

Access to 1- and 2-azabicyclo[x.y.0]alkanes by intramolecular cyclization of allylsilanes on α-acyliminium ions is described. This methodology is also used to achieve a highly stereoselective total synthesis of (±)-mesembrine.