Synthesis, Table of Contents PAPER © Georg Thieme Verlag Stuttgart ˙ New York Efficient Synthesis of the First N-Methyloxoarcyriaflavin Including an Original Central Seven-Membered Cycle Aurélie Bourderioux, Aziz Ouach, Valérie Bénéteau, Jean-Yves Mérour, Sylvain Routier*Institut de Chimie Organique et Analytique, (1) Université d’Orléans, (2) UMR CNRS 6005, Rue de Chartres, B.P. 6759, 45067 Orléans Cedex 2, FranceFax: +33(2)38417281; e-Mail: sylvain.routier@univ-orleans.fr; Recommend Article Abstract Buy Article All articles of this category Abstract A new route to the first N-methyloxoarcyriaflavin was designed. The compound was obtained by a palladium-catalyzed Stille cross-coupling reaction, followed by an electrophilic cyclization onto a C-2 indolic position as a key step. Key words indole - tropone - palladium - electrophilic cyclization - rearrangement Full Text References References 1a Sanchez C. Mendez C. Salas JA. Nat. Prod. Rep. 2006, 23: 1007 1b Knölker H.-J. Reddy KR. In The Alkaloids Vol. 65: Cordell GA. Elsevier Academic Press; New York: 2008. p.1-430 2a Sanchez-Martinez C. Shih C. Zhu G. Li T. Brooks HB. Patel BKR. Schultz RM. DeHahn TB. Spencer CD. Watkins SA. Ogg CA. Considine E. Dempsey JA. Zhang F. Bioorg. Med. Chem. Lett. 2003, 13: 3841 2b Zhu G. Conner SE. Zhou X. Shih C. Li T. Anderson BD. Brooks HB. Campbell RM. Considine E. Dempsey JA. Faul MM. Ogg C. Patel B. Schultz RM. Spencer CD. Teicher B. Watkins SA. J. Med. Chem. 2003, 46: 2027 3a Sanchez-Martinez C. Shih C. Faul MM. Zhu G. Paal M. Somoza C. Li T. Kumrich CA. Winneroski LL. Xun Z. Brooks HB. Patel BKR. Schultz RM. DeHahn TB. Spencer CD. Watkins SA. Considine E. Dempsey JA. Ogg CA. Campbell RM. Anderson BA. Wagner J. Bioorg. Med. Chem. Lett. 2003, 13: 3835 3b Engler TA. Furness K. Malhotra S. Sanchez-Martinez C. Shih C. Xie W. Zhu G. Zhou X. Conner S. Faul MM. Sullivan KA. Kolis SP. Brooks HB. Patel B. Schultz RM. DeHahn TB. Kirmani K. Spencer CD. Watkins SA. Considine EL. Dempsey JA. Ogg CA. Stamm NB. Anderson BD. Campbell RM. Vasudevan V. Lytle ML. Bioorg. Med. Chem. Lett. 2003, 13: 2261 3c Zhu G. Conner S. Zhou X. Shih C. Brooks HB. Considine E. Dempsey JA. Ogg C. Patel B. Schultz RM. Spencer CD. Teicher B. Watkins SA. Bioorg. Med. Chem. Lett. 2003, 13: 1231 3d Routier S. Peixoto P. Mérour J.-Y. Coudert G. Dias N. Bailly C. Pierré A. Léonce S. Caignard D.-H. J. Med. Chem. 2005, 48: 1401 3e Routier S. Mérour J.-Y. Dias N. Lansiaux A. Bailly C. Lozach O. Meijer L. J. Med. Chem. 2006, 49: 789 4a Caballero E. Adeva M. Calderon S. Sahagun H. Tomé F. Medarde M. Fernandez JL. Lopez-Lazaro M. Ayuso MJ. Bioorg. Med. Chem. 2003, 11: 3413 4b Pews-Davtyan A. Tillack A. Ortinau S. Rolfs A. Beller M . Org. Biomol. Chem. 2008, 6: 992 4c Levy DE. Wang D.-X. Lu Q. Chen Z. Perumattam J. Xu Y.-j. Liclican A. Higaki J. Dong H. Laney M. Mavunkel B. Dugar S. Bioorg. Med. Chem. Lett. 2008, 18: 2390 5a Bourderioux A. Routier S. Bénéteau V. Mérour J.-Y. Tetrahedron Lett. 2005, 46: 6071 5b Bourderioux A. Routier S. Bénéteau V. Mérour J.-Y. Tetrahedron 2007, 63: 9465 5c Bourderioux A. Bénéteau V. Mérour J.-Y. Baldeyrou B. Ballot C. Lansiaux A. Bailly C. Le Guével R. Guillouzo C. Routier S. Org. Biomol. Chem. 2008, 6: 2108 6 Su J.-Y. Zhu Y. Zeng L.-M. Xu X.-H. J. Nat. Prod. 1997, 60: 1043 7 Mahboobi S. Burgemeister T. Dove S. Kuhr S. Popp A. J. Org. Chem. 1999, 64: 8130 8 Brenner M. Mayer G. Terpin A. Steglich W. Chem. Eur. J. 1997, 3: 70 9a Steglich W. Steffan B. Kopanski L. Eckhardt G. Angew. Chem., Int. Ed. Engl. 1980, 19: 459 9b Brenner M. Rexhausen H. Steffan B. Steglich W. Tetrahedron 1988, 44: 2887 9c Faul MM. Sullivan KA. Winneroski LL. Synthesis 1995, 1511 10 Cruz MD. Jimenez F. Delgado F. Tamariz J. Synlett 2006, 749 11 Martin T. Moody CJ. J. Chem. Soc., Perkin Trans. 1 1988, 235 12 Mouaddib A. Joseph B. Hasnaoui A. Mérour J.-Y. Tetrahedron Lett. 1999, 40: 5853 13 Seebach D. Hungerbühler E. Naef R. Schnurrenberger P. Weidmann B. Züger M. Synthesis 1982, 138 14 Jacquemard U. Bénéteau V. Lefoix M. Routier S. Mérour J.-Y. Coudert G. Tetrahedron 2004, 60: 10039 15a Lucas H. Basten JEM. Van Dinther TG. Meuleman DG. Van Aelst SF. Van Boeckel CAA. Tetrahedron 1990, 46: 8207 15b Lopin C. Jacquinet J.-C. Angew. Chem. Int. Ed. 2006, 45: 2574 16a Robinson JR. Good NE. Can. J. Chem. 1957, 35: 1578 16b Sakamoto T. Nagano T. Kondo Y. Yamanaka H. Chem. Pharm. Bull. 1988, 36: 2248 17 Yang X. Xu X. Ji HF. J. Phys. Chem. B. 2008, 112: 7196 18 Conchon E. Aboab B. Golsteyn RM. Cruzalegui F. Edmonds T. Léonce S. Pfeiffer B. Prudhomme M. Eur. J. Med. Chem. 2006, 41: 1470 19a Vögeli U. Von Philipsborn W. Nagarajan K. Nair MD. Helv. Chim. Acta 1978, 61: 607 19b Chezal JM. Delmas G. Mavel S. Elakmaoui H. Métin J. Diez A. Blache Y. Gueiffier A. Rubiralta M. Teulade J.-C. Chavignon O. J. Org. Chem. 1997, 62: 4085 20 Wakchaure PB. Easwar S. Puranik VG. Argade NP. Tetrahedron 2008, 64: 1786 Supplementary Material Supplementary Material Supporting Information
