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Synthesis 2005(12): 1959-1966  
DOI: 10.1055/s-2005-869977
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Indolo[2,3-a]pyrrolo[3,4-c]carbazoles by Oxidative Cyclization of Bisindolylmaleimides with a Rhodium(III)-Copper(II) Catalytic System

Bernhard Witulski*, Torsten Schweikert
Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Correnstr. 40, 48143 Münster, Germany
Fax: +49(251)8336501; e-Mail: witulski@uni-muenster.de;
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Publication History

Received 12 January 2005
Publication Date:
24 June 2005 (online)

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Abstract

A novel catalytic protocol for the synthesis of a series of indolo[2,3-a]pyrrolo[3,4-c]carbazoles based on the bimetallic system RhCl3·3H2O and Cu(OAc)2·H2O in the presence of molecular oxygen was investigated. The method was applied to the synthesis of the glycosidated fluoroindolocarbazole 3 that was recently isolated as a metabolite from feeding experiments of Saccharothrix aerocolonigenes ATCC 39243 with fluorotryptophanes.

Key words

glycosides - rebeccamycin - catalysis - rhodium - copper

    References

  • For reviews on studies related to their chemistry and biology, see:
  • 1a Bergman J. Janosik T. Wahlström N. Adv. Heterocycl. Chem.  2001,  80:  1 
    CrossrefGoogle Scholar
  • 1b Pindur U. Kim Y.-S. Mehrabani F. Curr. Med. Chem.  1999,  6:  29 
    CrossrefGoogle Scholar
  • 1c Gribble GW. Berthel SJ. Studies in Natural Product Chemistry   Vol. 12:  . Elsevier Science Publishers; New York: 1993.  p.365 
    CrossrefGoogle Scholar
  • 1d Knölker HJ. Reddy KR. Chem. Rev.  2002,  102:  4303 
    CrossrefGoogle Scholar
  • 1e Steglich W. Pure Appl. Chem.  1989,  61:  281 
    CrossrefGoogle Scholar
  • 1f Prudhomme M. Curr. Pharm. Des.  1997,  3:  265 
    CrossrefGoogle Scholar
  • 1g Prudhomme M. Curr. Med. Chem.: Anti-Cancer Agents  2004,  4:  509 
    CrossrefGoogle Scholar
  • 2a Omura S. Iwai Y. Hirano A. Nakagawa A. Awaya J. Tsuchiya H. Takahashi Y. Masuma R. J. Antibiot.  1977,  30:  275 
    CrossrefPubMedGoogle Scholar
  • 2b Furusaki A. Hashiba N. Matsumoto T. J. Chem. Soc., Chem. Commun.  1978,  800 
    CrossrefPubMedGoogle Scholar
  • 2c Schupp P. Eder C. Proksch P. Wray VV. Schneider B. Herderich M. Paul V. J. Nat. Prod.  1999,  62:  959 
    CrossrefPubMedGoogle Scholar
  • For total syntheses, see:
  • 3a Link JT. Raghavan S. Danishefsky SJ. J. Am. Chem. Soc.  1995,  117:  552 
    CrossrefGoogle Scholar
  • 3b Link JT. Raghavan S. Gallant M. Chou TC. Ballas LM. Danishefsky SJ. J. Am. Chem. Soc.  1996,  118:  2825 
    CrossrefGoogle Scholar
  • 3c Wood JL. Stoltz BM. Goodman SN. J. Am. Chem. Soc.  1996,  118:  10656 
    CrossrefGoogle Scholar
  • 3d Wood JL. Stoltz BM. Goodman SN. Onwueme K. J. Am. Chem. Soc.  1997,  119:  9652 
    CrossrefGoogle Scholar
  • 4 Omura S, Iwai Y, and Hirano A. inventors; Japan Kokai  7873,501.  ; Chem. Abstr. 1978, 89, 178086h
  • 5 Oka S. Kodama M. Takeda H. Tomizuka N. Suzuki H. Agric. Biol. Chem.  1986,  50:  2723 
    Google Scholar
  • 6a Hung DT. Jamison TF. Schreiber SL. Chem. Biol.  1996,  3:  623 
    CrossrefGoogle Scholar
  • 6b Tamaoki T. Nomoto H. Takahashi I. Kato Y. Morimoto M. Tomita F. Biochem. Biophys. Res. Commun.  1986,  135:  397 
    CrossrefGoogle Scholar
  • 6c Yamada S. Hirota K. Chida K. Kuroki T. Biochem. Biophys. Res. Commun.  1988,  157:  9 
    CrossrefGoogle Scholar
  • 6d Fujita-Yamaguchi Y. Kathuria S. Biochem. Biophys. Res. Commun.  1988,  157:  955 
    CrossrefGoogle Scholar
  • 6e 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 
    CrossrefGoogle Scholar
  • 7a Bush JA. Long BH. Cationo JJ. Bradner WT. Tomita K. J. Antibiot.  1987,  40:  668 
    CrossrefGoogle Scholar
  • 7b Nettleton DE. Doyle TW. Krishnan B. Matsumoto GK. Clardy J. Tetrahedron Lett.  1985,  26:  4011 
    CrossrefGoogle Scholar
  • 7c Pommier Y. Curr. Med. Chem.: Anti-Cancer Agents  2004,  4:  429 
    CrossrefGoogle Scholar
  • 7d Voldoire A. Moreau P. Sancelme M. Matulova M. Léonce S. Pierré A. Hickman J. Pfeiffer B. Renard P. Dias N. Bailly C. Prudhomme M. Bioorg. Med. Chem.  2004,  12:  1955 
    CrossrefGoogle Scholar
  • 7e Woo MH. Vance JR. Otero Marcos AR. Bailly C. Bjornsti M.-A. J. Biol. Chem.  2002,  277:  3813 
    CrossrefGoogle Scholar
  • 7f Moreau P. Anizon F. Sancelme M. Prudhomme M. Sevère D. Riou J.-F. Goossens J.-F. Hénichart J.-P. Bailly C. Labourier E. Tazzi J. Fabbro D. Meyer T. Aubertin AM. J. Med. Chem.  1999,  42:  1816 
    CrossrefGoogle Scholar
  • 7g Bailly C. Riou J.-F. Colson P. Houssier C. Rodrigues-Pereira E. Prudhomme M. Biochemistry  1997,  36:  3917 
    CrossrefGoogle Scholar
  • 7h Faul MM. Sullivan KA. Grutsch JL. Winneroski LL. Shih C. Sanchez-Martinez C. Cooper JT. Tetrahedron Lett.  2004,  45:  1095 
    CrossrefGoogle Scholar
  • For total syntheses of rebeccamycin, see:
  • 8a Kaneko T. Wong H. Okamoto KT. Clardy J. Tetrahedron Lett.  1985,  26:  4015 
    CrossrefGoogle Scholar
  • 8b Gallant M. Link JT. Danishefsky SJ. J. Org. Chem.  1993,  58:  343 
    CrossrefGoogle Scholar
  • 8c Faul MM. Winneroski LL. Krumrich CA. J. Org. Chem.  1999,  64:  2465 
    CrossrefGoogle Scholar
  • 9 Lam KS. Schroeder DR. Veitch JM. Colson KL. Matson JA. Rose WC. Doyle TW. Forenza S. J. Antibiot.  2001,  54:  1 
    CrossrefGoogle Scholar
  • 10 Long BH. Rose WC. Vyas DM. Matson JA. Forenza S. Curr. Med. Chem.: Anti-Cancer Agents  2002,  2:  255 
    CrossrefGoogle Scholar
  • 11 For the assembly of indolo[2,3-a]carbazoles via metalation-cross-coupling sequences, see: Cai X. Snieckus V. Org. Lett.  2004,  6:  2293 
    CrossrefGoogle Scholar
  • 12 For the assembly of indolo[2,3-a]carbazoles via Pd-mediated endo-dig cyclizations, see: Saulnier MG. Frennesson DB. Deshpande MS. Vyas DM. Tetrahedron Lett.  1995,  36:  7841 
    CrossrefGoogle Scholar
  • 13 For the assembly of indolo[2,3-a]carbazoles via chromium carbene complexes, see: Merlic CA. McInnes DM. You Y. Tetrahedron Lett.  1997,  38:  6787 
    CrossrefGoogle Scholar
  • For the assembly of indolo[2,3-a]carbazoles by Diels-Alder reactions, see:
  • 14a Kuethe JT. Davies IW. Tetrahedron Lett.  2004,  45:  4009 
    Google Scholar
  • 14b Pindur U. Kim M.-H. Arch. Pharm.  1992,  325:  353 
    Google Scholar
  • 14c Nomak R. Snyder JK. Tetrahedron Lett.  2001,  42:  7929 
    Google Scholar
  • 14d Barry JF. Wallace TW. Walshe NDA. Tetrahedron  1995,  47:  12797 
    Google Scholar
  • For approaches to the indolo[2,3-a]carbazole ring system by double Fischer indolizations, see:
  • 15a Bergman J. Pelcman B. J. Org. Chem.  1989,  54:  824 
    CrossrefGoogle Scholar
  • 15b Gribble GW. Berthel SJ. Tetrahedron  1992,  48:  8869 
    CrossrefGoogle Scholar
  • 16a Link JT. Gallant M. Danishefsky SJ. Huber S. Tetrahedron Lett.  1994,  35:  5555 
    CrossrefGoogle Scholar
  • 16b Beccalli EM. Gelmi ML. Marchesini A. Tetrahedron  1998,  54:  6909 
    CrossrefGoogle Scholar
  • 16c Eils S. Winterfeldt E. Synthesis  1999,  275 
    CrossrefGoogle Scholar
  • 16d Routier S. Coudert G. Mérour J.-Y. Caignard DH. Tetrahedron Lett.  2002,  43:  2561 
    CrossrefGoogle Scholar
  • 16e Reddy GM. Chen S.-Y. Uang B.-J. Synthesis  2003,  497 
    CrossrefGoogle Scholar
  • 16f Sanchez-Martinez C. Faul MM. Shih C. Sullivan KA. Grutsch JL. Cooper JT. Kolis SP. J. Org. Chem.  2003,  68:  8008 
    CrossrefGoogle Scholar
  • 17a Joyce RP. Gainor JA. Weinreb SM. J. Org. Chem.  1987,  52:  1177 
    CrossrefGoogle Scholar
  • 17b Kleinschroth J. Hartenstein J. Rudolph C. Schächtele C. Bioorg. Med. Chem. Lett.  1995,  5:  55 
    CrossrefGoogle Scholar
  • 17c Chisholm JD. Van Vranken DL. J. Org. Chem.  2000,  65:  7541 
    CrossrefGoogle Scholar
  • 17d 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 
    CrossrefGoogle Scholar
  • 18 Faul MM. Sullivan KA. Tetrahedron Lett.  2001,  42:  3271 
    CrossrefGoogle Scholar
  • 19a Harris W. Hill CH. Keech E. Malsher P. Tetrahedron Lett.  1993,  34:  8361 
    CrossrefGoogle Scholar
  • 19b Beccalli EM. Gelmi ML. Marchesini A. Tetrahedron  1998,  54:  6909 
    CrossrefGoogle Scholar
  • 20 Ohkubo M. Nishimura T. Jona H. Honma T. Morishima H. Tetrahedron  1996,  52:  8099 
    CrossrefGoogle Scholar
  • 21a Ohkubo M. Kawamoto H. Ohno T. Nakano M. Morishima H. Tetrahedron  1997,  53:  585 
    CrossrefGoogle Scholar
  • 21b Zembower DE. Zhang H. Lineswala JP. Kuffel MJ. Aytes SA. Ames MM. Bioorg. Med. Chem. Lett.  1999,  9:  145 
    CrossrefGoogle Scholar
  • 22 Ohkubo M. Nishimura T. Jona H. Honma T. Ito S. Morishima H. Tetrahedron  1997,  53:  5937 
    CrossrefGoogle Scholar
  • 23 Wang J. Rosingana M. Watson DJ. Dowdy ED. Discordia RP. Soundarajan N. Li W.-S. Tetrahedron Lett.  2001,  42:  8935 
    CrossrefGoogle Scholar
  • 24a Steglich W. Steffan B. Kopanski L. Eckhardt G. Angew. Chem., Int. Ed. Engl.  1980,  19:  459 
    CrossrefGoogle Scholar
  • 24b Brenner M. Rexhausen H. Steffan B. Steglich W. Tetrahedron  1988,  44:  2887 
    CrossrefGoogle Scholar
  • 25 Grushin VV. Marshall WJ. Thorn DL. Adv. Synth. Catal.  2001,  343:  161 
    CrossrefGoogle Scholar
  • 26a Kalinovskii IO. Lescheva AA. Kuteinikova MM. Gel’bshtein AI. Zh. Obshch. Khim.  1990,  60:  123 ; J. Gen. Chem. USSR (Engl. Transl.), 1990, 60, 108
    Google Scholar
  • 26b Leshcheva AA. Kalinovskii IO. Pogorelov VV. Noskov YG. Gel’bshtein AI. Kin. Katal.  1998,  39:  354 
    Google Scholar
  • 27 Choi D.-S. Huang S. Huang M. Barnard TS. Adams RD. Seminario JM. Tour JM. J. Org. Chem.  1998,  63:  2646 
    CrossrefGoogle Scholar
  • 28 Bergman J. Koch E. Pelcman B. J. Chem. Soc., Perkin Trans. 1  2000,  2609 
    CrossrefGoogle Scholar
  • 29 When this manuscript was in preparation, we became aware of a recent report on the design, synthesis and biological evaluation of a set of fluoroindolocarbazole glycosides including compound 3 as very selective topoisomerase I active agents. However, no experimental details were given: Balasubramanian BN. St. Laurent DR. Saulnier MG. Long BH. Bachand C. Beaulieu F. Clarke W. Deshpande M. Eummer J. Fairchild CR. Frennesson DB. Kramer R. Lee FY. Mahler M. Martel A. Naidu BN. Rose WC. Russell J. Ruediger E. Solomon C. Stoffan KM. Wong H. Zimmermann K. Vyas DM. J. Med. Chem.  2004,  47:  1609 
    CrossrefGoogle Scholar