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Synthesis 2012(2): 297-303  
DOI: 10.1055/s-0031-1289648
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Concise and Diastereoselective Synthesis of Piperidine and Indolizidine Alkaloids via Aza-Prins Cyclization

Basi V. Subba Reddy*a, Dudhmal N. Chayaa, Jhillu S. Yadava, René Gréeb
a Discovery Laboratory, Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)27160512; e-Mail: basireddy@iict.res.in; e-Mail: bvsreddiict@gmail.com;
b Université de Rennes 1, Laboratoire SCR, CNRS UMR 6226, Avenue du Général Leclerc, 35042 Rennes Cedex, France
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Publication History

Received 27 September 2011
Publication Date:
15 December 2011 (online)

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Abstract

The synthesis of 2-substituted and 2,4-disubstituted piperidine alkaloids such as (±)-coniine, (±)-hydroxypipecolic acid, (±)-pipecolic acid, (±)-coniceine, and (±)-4-hydroxy-2-hydroxy­methyl piperidine have been accomplished in a highly diastereo­selective manner by employing aza-Prins cyclization as a key step to construct the piperidine core of these alkaloids.

Key words

aza-Prins cyclization - diastereoselective - piperidine - alkaloids - natural products

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