Synthesis, Table of Contents 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, FranceFax: +33(4)72431214; e-Mail: benoit.joseph@univ-lyon1.fr; Recommend Article Abstract Buy Article All articles of this category 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. Key words indoles - metalation - regioselectivity - addition reactions - palladium Full Text References References 1a Casapullo A. Bifulco G. Bruno I. Riccio R. J. Nat. Prod. 2000, 63: 447 1b Faulkner DJ. Nat. Prod. Rep. 2002, 19: 1 2 Jacobs RS, Pomponi S, Gunasekera S, and Wright A. inventors; PCT Int. Appl. WO 9818466. ; Chem. Abstr. 1998, 129, 587 3 Montagne C. Fournet G. Joseph B. Synlett 2003, 1533 4 Iddon B. Lim BL. J. Chem. Soc., Perkin Trans. 1 1983, 735 5 Kimura R. Nagano T. Kinoshita H. Bull. Chem. Soc. Jpn. 2002, 75: 2517 6 Iddon B. Ngochindo RI. Heterocycles 1994, 38: 2487 7 Koya K, Sun L, Ono M, James D, Ying W, and Chen S. inventors; PCT Int. Appl. WO 03022274. ; Chem. Abstr. 2003, 138, 238183 8 Miyaura N. Suzuki A. Chem. Rev. 1995, 95: 2457 9 Fürstner A. Grabowski J. Lehmann CW. Katoaka T. Nagai K. ChemBiochem 2001, 2: 60 ; and references cited therein 10 Young EHP. J. Chem. Soc. 1958, 3493 11 Allen MS. Hamaker LK. La Loggia AJ. Cook JM. Synth. Commun. 1992, 22: 2077