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

Laurent De Buyck; Rita Cagnoli; Franco Ghelfi; Giulia Merighi; Adele Mucci; Ugo M. Pagnoni; Andrew F. Parsons

doi:10.1055/s-2004-829116

PAPER

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

Laurent De Buyck*^a, Rita Cagnoli^b, Franco Ghelfi*^b, Giulia Merighi^b, Adele Mucci^b, Ugo M. Pagnoni^b, Andrew F. Parsons^c
^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

Abstract

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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

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References

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