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Synthesis 2011(22): 3711-3715  
DOI: 10.1055/s-0030-1260248
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

New Efficient Synthesis of Combretastatin A-4 via Colvin Rearrangement

Ognyan I. Petrov*a, Mariana S. Gerovaa, Christo D. Chaneva, Katya V. Petrovab
a Faculty of Chemistry, University of Sofia St. Kliment Ohridski, 1 James Bourchier Avenue, 1164 Sofia, Bulgaria
Fax: +359(2)9625438; e-Mail: opetrov@chem.uni-sofia.bg;
b Chemistry Department, Vanderbilt University, Nashville, TN 37235-1822, USA
Further Information

Publication History

Received 21 July 2011
Publication Date:
29 September 2011 (online)

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Abstract

A new four-step approach for the synthesis of anticancer agent combretastatin A-4 (CA-4) has been developed. The method includes the Colvin rearrangement of the benzophenone derivative phenstatin to the key diarylalkyne followed by stereoselective semi-reduction to CA-4 in good overall yield.

Key words

combretastatin A-4 - phenstatin - Colvin rearrangement - anticancer agents - stilbene

    References

  • 1 Pettit GR. Singh SB. Hamel E. Lin CM. Alberts DS. Garcia-Kendall D. Experientia  1989,  45:  209 
    CrossrefSearch in Google Scholar
  • 2a Lin CM. Ho HH. Pettit GR. Hamel E. Biochemistry  1989,  28:  6984 
    Search in Google Scholar
  • 2b Young SL. Chaplin DJ. Expert Opin. Investig. Drugs  2004,  13:  1171 
    Search in Google Scholar
  • 3a Tozer GM. Prise VE. Wilson J. Locke RJ. Vojnovic B. Stratford MR. Dennis MF. Chaplin DJ. Cancer Res.  1999,  59:  1626 
    Search in Google Scholar
  • 3b Stevenson JP. Rosen M. Sun W. Gallagher M. Haller DG. Vaughn D. Giantonio B. Zimmer R. Petros WP. Stratford M. Chaplin D. Young SL. Schnall M. O’Dwyer PJ. J. Clin. Oncol.  2003,  21:  4428 
    Search in Google Scholar
  • 3c Kanthou C. Greco O. Stratford A. Cook I. Knight R. Benzakour O. Tozer G. Am. J. Pathol.  2004,  165:  1401 
    Search in Google Scholar
  • 3d Vincent L. Kermani P. Young LM. Cheng J. Zhang F. Shido K. Lam G. Vincent HB. Zhu Z. Hicklin DJ. Bohlen P. Chaplin DJ. May C. Rafii S. J. Clin. Investig.  2005,  115:  2992 
    Search in Google Scholar
  • 4 Vitale I. Antoccia A. Cenciarelli C. Crateri P. Meschini S. Arancia G. Pisano C. Tanzarella C. Apoptosis  2007,  12:  155 
    CrossrefSearch in Google Scholar
  • 5 Lin HL. Chiou SH. Wu CW. Lin WB. Chen LH. Yang YP. Tsai ML. Uen YH. Liou JP. Chi CW. J. Pharmacol. Exp. Ther.  2007,  323:  365 
    CrossrefSearch in Google Scholar
  • 6 Petit I. Karajannis MA. Vincent L. Young L. Butler J. Hooper AT. Shido K. Steller H. Chaplin DJ. Feldman E. Rafii S. Blood  2008,  111:  1951 
    CrossrefSearch in Google Scholar
  • 7 Shen CH. Shee JJ. Wu JY. Lin YW. Wu JD. Liu YW. Br. J. Pharmacol.  2010,  160:  2008 
    CrossrefSearch in Google Scholar
  • 8a Pettit GR. Singh SB. Boyd MR. Hamel E. Pettit RK. Schmidt JM. Hogan F. J. Med. Chem.  1995,  38:  1666 
    Search in Google Scholar
  • 8b Gaukroger K. Hadfield JA. Hepworth LA. Lawrence NJ. McGown AT. J. Org. Chem.  2001,  66:  8135 
    Search in Google Scholar
  • 8c Camacho-Dávila AA. Synth. Commun.  2008,  38:  3823 
    Search in Google Scholar
  • 8d Singh R. Kaur N. Synthesis  2009,  2471 
  • 8e Chen Y. Zou Y. Sun H.-Y. Liu X.-K. Xiao C.-F. Sun J. He S.-J. Li J. Synthesis  2011,  217 
  • 9 Fürstner A. Nikolakis K. Liebigs Ann. Chem.  1996,  2107 
  • 10 Lawrence NJ. Ghani FA. Hepworth LA. Hadfield JA. McGown AT. Pritchard RG. Synthesis  1999,  1656 
    Thieme Connect
  • 11 Giraud A. Provot O. Hamzé A. Brion J.-D. Alami M. Tetrahedron Lett.  2008,  49:  1107 
    CrossrefSearch in Google Scholar
  • 12 Lara-Ochoa F. Espinosa-Pérez G. Tetrahedron Lett.  2007,  48:  7007 
    CrossrefSearch in Google Scholar
  • 13 Colvin EW. Hamill BJ. J. Chem. Soc., Perkin Trans. 1  1977,  869 
  • 14 Miwa K. Aoyama T. Shioiri T. Synlett  1994,  107 
    Thieme Connect
  • 15 Wu M. Ji Q. Yang Q. Xie Y. Org. Prep. Proced. Int.  2005,  37:  272 
    CrossrefSearch in Google Scholar
  • 16 Majumder PL. Joardar M. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.  1984,  23:  1040 
    Search in Google Scholar
  • 17 Eaton PE. Carlson GR. Lee JT. J. Org. Chem.  1973,  38:  4071 
    CrossrefSearch in Google Scholar
  • 18 Pettit GR. Toki B. Herald DL. Verdier-Pinard P. Boyd MR. Hamel E. Pettit RK. J. Med. Chem.  1998,  41:  1688 
    CrossrefSearch in Google Scholar
  • 19 Zou Y. Xiao C.-F. Zhong R.-Q. Wei W. Huang W.-M. He S.-J. J. Chem. Res.  2008,  354