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Synthesis 2011(15): 2478-2482  
DOI: 10.1055/s-0030-1260117
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

N-tert-Butanesulfinyl Imines in Alkaloid Synthesis: Stereoselective Synthesis of (R)-Coniine and Formal Synthesis of (S)-δ-Coniceine [¹]

Kongara Damodar, Maram Lingaiah, Nisith Bhunia, Biswanath Das*
Organic Chemistry Division-1, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160512; e-Mail: biswanathdas@yahoo.com;
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Publication History

Received 14 April 2011
Publication Date:
14 July 2011 (online)

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Abstract

A stereoselective synthesis of the hemlock alkaloid (R)-coniine and a formal synthesis of the indolizidine alkaloid (S)-δ-coniceine were achieved by means of a highly diastereoselective Barbier-type indium-mediated allylation strategy involving (S)-(N-tert-butanesulfinyl)imines.

Key words

alkaloids - stereoselective synthesis - piperidines

1

Part 49 in the series ‘Synthetic Studies on Natural Products’.

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1

Part 49 in the series ‘Synthetic Studies on Natural Products’.