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Note | Regular issue | Vol 53, No. 6, 2000, pp.1371-1378
Published online, 1st January, 1970
DOI: 10.3987/COM-00-8883
Synthesis of Enantiopure 8-Aminomethylindolizines from Glutamine by Stereoelectronically Controlled Cationic Cyclization

Thomas Lehmann and Peter Gmeiner*

*Department of Medicinal Chemistry, Emil Fischer Center, Friedrich-Alexander University, Schuhstraße 19, D-91052 Erlangen, Germany

Abstract

Starting from natural glutamine the synthesis of the 8-aminomethylindolizine (4b) was accomplished. The construction of the ring system was performed by employing a cationic 6-exo π-cyclization of an intermediate aziridinium salt. Transformation of the N,N-dibenzyl protected amine (4b) into the pharmacologically relevant target compound (11) is also describcd.