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Synthesis 2004(10): 1680-1686  
DOI: 10.1055/s-2004-829116
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Simple and Efficient Route to Chaetomellic Anhydride A: A Potent Natural Ras Farnesyl-Protein Transferase Inhibitor

Laurent De Buyck*a, Rita Cagnolib, Franco Ghelfi*b, Giulia Merighib, Adele Muccib, Ugo M. Pagnonib, Andrew F. Parsonsc
a Department of Organic Chemistry, Faculty of Agricultural and Applied Biological Sciences, University of Gent, Coupure Links 653, 9000 Gent, Belgium
b Dipartimento di Chimica, Università degli Studi di Modena e Reggio Emilia, via Campi 183, 41100 Modena, Italy
Fax: +39(59)373543; e-Mail: ghelfi.franco@unimo.it;
c Department of Chemistry, University of York, Heslington, York YO10 5DD, United Kingdom
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Publication History

Received 1 March 2004
Publication Date:
23 June 2004 (online)

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Abstract

A new and efficient approach to chaetomellic anhydride A has been devised starting from 2,2-dichloropalmitic acid. This involves the atom transfer radical cyclization of an N-alkyl-N-(3-chloro-2-propenyl)amide followed by rearrangement of the resulting trichloro-pyrrolidin-2-one.

Key words

amides - cyclisations - halogenation - pyrrolidinones - radical reactions