Synlett 1991; 1991(8): 589-591
DOI: 10.1055/s-1991-20808
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Chiral Acyliminium Ions in Alkaloid Synthesis: Stereospecific Formation of a (R)-12b-Indoloquinolizidinone

A. Pancrazi* , J. Kervagoret, Q. Khuong-Huu
  • *Institut de Chimie des Substances Naturelles, CNRS, F-91198 Gif sur Yvette, France
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Publication History

Publication Date:
07 March 2002 (online)

Methyl 2,3-dideoxy-3-C-(methoxycarbonylmethyl)-α/β-D-erythro-pento-5-aldofuranosides and tryptamine were submitted to a Pictet-Spengler condensation to give the (3aR,13bR,13cS)-2,3,3a,4,5,7,8,13,13b, 13c-decahydro-5-oxofuro[2,3-a]indolo[3,2-h]-quinolizine in a stereospecific way via an acyliminium ion intermediate.

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