Synlett 2014; 25(19): 2791-2793
DOI: 10.1055/s-0034-1379305
letter
© Georg Thieme Verlag Stuttgart · New York

Friedel–Crafts Cyclodehydration Approach toward the Synthesis of Ellipti-cine and 9-Methoxyellipticine

Nagarajan Ramkumar
School of Chemistry, University of Hyderabad, Hyderabad 500 046, India   Fax: +91(40)23012460   Email: rnsc@uohyd.ernet.in
,
Medishetty S. Raghavendra
School of Chemistry, University of Hyderabad, Hyderabad 500 046, India   Fax: +91(40)23012460   Email: rnsc@uohyd.ernet.in
,
Rajagopal Nagarajan*
School of Chemistry, University of Hyderabad, Hyderabad 500 046, India   Fax: +91(40)23012460   Email: rnsc@uohyd.ernet.in
› Author Affiliations
Further Information

Publication History

Received: 21 August 2014

Accepted after revision: 21 September 2014

Publication Date:
20 October 2014 (online)


Abstract

An expedient synthesis of biologically important pyrido[4,3-b]carbazole alkaloids, ellipticine and 9-methoxyellipticine, is reported. Our synthetic approach applies a key H3PO4-mediated Friedel–Crafts cyclodehydration to construct the pyridine core.

Supporting Information

 
  • References and Notes

    • 1a Knölker H.-J, Reddy KR In The Alkaloids . Vol. 65. Cordell GA. Elsevier Science; Amsterdam: 2008: 1-430
    • 1b Álvarez M, Joule JA In The Alkaloids . Vol. 57. Cordell GA. Academic Press; New York: 2001: 235
    • 1c Gribble GW In Advances in Heterocyclic Natural Product Synthesis . Vol. 1. Pearson WH. JAI Press; Greenwich, CT: 1990: 43
    • 1d Gribble GW In The Alkaloids . Vol. 39. Brossi A. Academic Press; New York: 1990: 239
  • 2 Goodwin S, Smith AF, Horning EC. J. Am. Chem. Soc. 1959; 81: 1903
    • 3a Woodward RB, Iacobucci GA, Hochstein FA. J. Am. Chem. Soc. 1959; 81: 4434
    • 3b Svoboda GH, Poore GA, Montfort ML. J. Pharm. Sci. 1968; 57: 1720
    • 3c Kilminster KN, Sainsbury M, Webb B. Phytochemistry 1972; 11: 389
    • 3d Ahond A, Fernandez H, Julia-Moore M, Poupat C, Sanchez V, Potier P, Kan SK, Sevenet T. J. Nat. Prod. 1981; 44: 193
    • 3e Lin Y.-M, Juichi M, Wu R.-Y, Lee K.-H. Planta Med. 1985; 51: 545
    • 4a Juret P, Tanguy A, Girard A, Le Talaer JY, Abbatucci JS, Dat-Xuong N, Le Pecq JB, Paoletti C. Eur. J. Cancer 1978; 14: 205
    • 4b Paoletti C, Le Pecq L.-B, Dat-Xuong N, Juret P, Garnier H, Amiel J.-L, Rouesse J. Recent Res. Cancer Res. 1980; 74: 107
    • 4c Dodion P, Rozencweig M, Nicaise C, Piccart M, Cumps E, Crespeigne N, Kisner D, Kenis Y. Eur. J. Cancer Clin. Oncol. 1982; 18: 519
    • 4d Juret P, Heron JF, Couette JE, Delozier T, Le Talaer JY. Cancer Treat. Rep. 1982; 66: 1909
    • 4e Clarysse A, Brugarolas A, Siegenthaler P, Abele R, Cavalli F, de Jager R, Renard G, Rozencweig M, Hansen HH. Eur. J. Cancer Clin. Oncol. 1984; 20: 243
    • 6a Stiborová M, Bieler CA, Wiessler M, Frei E. Biochem. Pharmacol. 2001; 62: 1675
    • 6b Stiborová M, Sejbal J, Borek-Dohalská L, Aimová D, Poljaková J, Forsterová K, Rupertová M, Wiesner J, Hudeček J, Wiessler M, Frei E. Cancer Res. 2004; 64: 8374
    • 7a Miller CM, McCarthy FO. RSC Adv. 2012; 2: 8883
    • 7b Schmidt AW, Reddy KR, Knölker H.-J. Chem. Rev. 2012; 112: 3193
    • 7c Deane FM, O’Sullivan EC, Maguire AR, Gilbert J, Sakoff JA, McCluskey A, McCarthy FO. Org. Biomol. Chem. 2013; 11: 1334
    • 8a Mal D, Senapati BK, Pahari P. Tetrahedron 2007; 63: 3768
    • 8b Mal D, Senapati BK, Pahari P. Synlett 2005; 994
    • 8c Miki Y, Tsuzaki Y, Hibino H, Aoki Y. Synlett 2004; 2206
    • 8d Miki Y, Aoki Y, Tsuzaki Y, Umemoto M, Hibino H. Heterocycles 2005; 65: 2693
    • 8e Bennasar ML, Roca T, Ferrando F. J. Org. Chem. 2005; 70: 9077
    • 8f Pedersen JM, Bowman WR, Elsegood MR. J, Fletcher AJ, Lovell PJ. J. Org. Chem. 2005; 70: 10615
    • 8g Ho T.-L, Hsieh S.-Y. Helv. Chim. Acta 2006; 89: 111
    • 8h Liu C.-Y, Knochel P. J. Org. Chem. 2007; 72: 7106
    • 8i Konakahara T, Kiran YB, Okuno Y, Ikeda R, Sakai N. Tetrahedron Lett. 2010; 51: 2335
    • 8j Yokoyama Y, Okuyama N, Iwadate S, Momoi T, Murakami Y. J. Chem. Soc., Perkin Trans. 1 1990; 1319
    • 8k Ramkumar N, Nagarajan R. J. Org. Chem. 2014; 79: 736
    • 8l Watanabe M, Snieckus V. J. Am. Chem. Soc. 1980; 102: 1457
  • 9 Cranwell PA, Saxton JE. J. Chem. Soc. 1962; 3482
    • 10a Jackson AH, Jenkins PR, Shannon PV. R. J. Chem. Soc., Perkin Trans. 1 1977; 1698
    • 10b Jackson A, Wilson ND. V, Gaskell AJ, Joule JA. J. Chem. Soc. C 1969; 2738
  • 11 Lee H.-Y, Chen GS, Chen C.-S, Chern J.-W. J. Heterocycl. Chem. 2010; 47: 454
  • 12 Dračínský M, Sejbal J, Rygerová B, Stiborová M. Tetrahedron Lett. 2007; 48: 6893
    • 13a Movassaghi M, Hill MD. Org. Lett. 2008; 10: 3485
    • 13b Saito S, Sato Y, Ohwada T, Shudo K. J. Am. Chem. Soc. 1994; 116: 2312
    • 13c Saito S, Ohwada T, Shudo K. J. Am. Chem. Soc. 1995; 117: 11081
    • 13d Low C.-E, Roberts RM. J. Org. Chem. 1973; 38: 1909
    • 13e Bailey D, De Grazia CG. J. Org. Chem. 1970; 35: 4093
    • 13f Bradsher CK. Chem. Rev. 1946; 38: 447
  • 14 The CCDC deposition number for compound 19 is 994825. Formula: C24H20N2. Unit cell parameters: a = 15.225 (8), b = 5.364 (3), c = 22.108 (12), α = 90, β = 101.789 (9), γ = 90, Space group P21/c.