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Paper | Special issue | Vol 67, No. 1, 2006, pp.205-214
Published online, 12th August, 2005
DOI: 10.3987/COM-05-S(T)13
From Amino Acids to Polycyclic Heterocycles - Synthesis of Enantiopure, Functionally Diverse Isopavines and Dihydromethanodibenzoazocines

Stephen Hanessian,* Clément Talbot, Marc Mauduit, Parthasarathy Saravanan, and Jayapal Reddy Gone

*Department of Chemistry, University of Montreal, 2900 Edouard-Montpetit, Montréal, Québec H3C 3J7, Canada

Abstract

The intramolecular double Friedel-Crafts condensation of N,N-dibenzyl-O-benzyl-L-threoninal affords a rearranged tetracyclic compound involving a methyl migration. N-Demethylation of tetracyclic isopavines leads to topologically unique secondary amines with potential utility in catalytic reactions as a chiral basic ligand.