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Synthesis 2002(1): 0111-0115
DOI: 10.1055/s-2002-19302
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Convenient Route to Alkaloid Lipids: Application for the Synthesis of a Leptophylline A Analogue

Sofia D. Koulocheria, Emmanuel N. Pitsinosb, Serkos A. Haroutounian*a
a Chemistry Laboratory, Agricultural University of Athens, Iera Odos 75, Athens 11855, Greece
Fax: +30(1)5294265; e-Mail: sehar@aua.gr;
b Laboratory of Organic and Bioorganic Chemistry, Institute of Physical Chemistry, NCSR ”Demokritos", P.O. Box 60228, Athens 15310, Greece
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Publication History

Received 31 July 2001
Publication Date:
04 August 2004 (online)

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Abstract

A synthetic route for efficient access to alkaloid lipids, using the chiral 2,3,6-trisubstituted piperidine acetaldehyde 9 as an intermediate, is reported. The utility of the synthetic route was demonstrated in the asymmetric synthesis of an unnatural analogue of Cassia leptophylla alkaloid lipid, leptophyllin A, in 16 steps and 15% overall yield starting from d-glucal.

Key words

piperidines - alkaloids - asymmetric synthesis