Synthesis 2005(1): 136-146  
DOI: 10.1055/s-2004-834905
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Homocarbonyltopsentine Derivatives

Cyril Montagne, Guy Fournet, Benoît Joseph*
Laboratoire de Chimie Organique 1, UMR-CNRS 5181, Université Claude Bernard - Lyon 1, CPE - Bâtiment 308, 43 Boulevard du 11 Novembre 1918, 69622 Villeurbanne Cedex, France
Fax: +33(4)72431214; e-Mail: benoit.joseph@univ-lyon1.fr;
Further Information

Publication History

Received 14 July 2004
Publication Date:
02 November 2004 (online)

Abstract

Homocarbonyltopsentines I are known to exhibit interesting anti-inflammatory activity in vivo. In order to study the role of the heterocycles in the modulation of their activity, several analogues in which indoles were replaced either by substituted indoles or by bioisosteric heterocycles such as pyrrolo[2,3-b]pyridine, benzo[b]thiophene and pyridine were synthesised. The synthesis is based on selective halogen-metal exchange on triiodoimidazole 1 and subsequent addition to formylated heterocycles.