Synthesis 2007(6): 929-935  
DOI: 10.1055/s-2007-965935
PAPER
© Georg Thieme Verlag Stuttgart · New York

A General Route to 4-C-Substituted Pyrimidine Nucleosides

Ulrich Hennecke, David Kuch, Thomas Carell*
Fakultät für Chemie und Pharmazie, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13 Haus F, 81377 München, Germany
Fax: +49(89)218077756; e-Mail: thomas.carell@cup.uni-muenchen.de;
Further Information

Publication History

Received 2 November 2006
Publication Date:
13 February 2007 (online)

Abstract

Palladium-catalyzed cross-coupling reactions of tin and zinc nucleophiles with arylsulfonates of pyrimidine nucleosides have been achieved to give a wide range of 4-C-substituted pyrimidine nucleosides. This method also allows the construction of pyrimidine-pyrimidinone dinucleosides, containing the carbon skeleton of the (6-4) DNA photo lesion.

    References

  • 1 Galmarini CM. Jordheim L. Dumontet C. Exp. Rev. Anticancer Therapy  2003,  3:  717 
  • 2 Jeong LS. Lee JA. Antiviral Chem. Chemother.  2004,  15:  235 
  • 3 Gao K. Orgel LE. Nucleosides, Nucleotides Nucleic Acids  2000,  19:  935 
  • 4 Berber H. Soufyane M. Mirand C. Schmidt S. Aubertin AM. Tetrahedron  2001,  57:  7369 
  • 5 Friedel MG. Cichon MK. Carell T. In CRC Handbook of Organic Photochemistry and Photobiology   2nd ed.:  Horspool WM. CRC Press; Boca Raton: 2004.  p.141/1 
  • 6 Sekine M. J. Org. Chem.  1989,  54:  2321 
  • 7 Ding Y. Habib Q. Shaw SZ. Li DY. Abt JW. Hong Z. An H. J. Comb. Chem.  2003,  5:  851 
  • 8 Bischofberger N. Tetrahedron Lett.  1987,  28:  2821 
  • 9 Bischofberger N. Tetrahedron Lett.  1989,  30:  1621 
  • 10 Havelkova M. Dvorak D. Hocek M. Synthesis  2001,  1704 
  • 11 Capek P. Pohl R. Hocek M. Org. Biomol. Chem.  2006,  4:  2278 
  • 12 Hocek M. Naus P. Pohl R. Votruba I. Furman PA. Tharnish PM. Otto MJ. J. Med. Chem.  2005,  48:  5869 
  • 13 Lakshman MK. Thomson PF. Nuqui MA. Hilmer JH. Sevova N. Boggess B. Org. Lett.  2002,  4:  1479 
  • 14 Lakshman MK. Gunda P. Pradhan P. J. Org. Chem.  2005,  70:  10329 
  • 15 Acevedo OL. Andrews RS. Dunkel M. Cook PD.
    J. Heterocycl. Chem.  1994,  31:  989 
  • 16 Switzer C. Shin D. Chem. Commun.  2005,  1342 
  • 17 Stille JK. Angew. Chem., Int. Ed. Engl.  1986,  25:  508 
  • 18 Hayashi T. Konishi M. Kobori Y. Kumada M. Higuchi T. Hirotsu K. J. Am. Chem. Soc.  1984,  106:  158 
  • 19 Palmisano G. Santagostino M. Tetrahedron  1993,  49:  2533 
  • 20 Naus P. Votruba I. Hocek M. Collect. Czech. Chem. Commun.  2004,  69:  1955 
  • 21 Kunieda T. Witkop B. J. Am. Chem. Soc.  1971,  93:  3478 
  • 22 Coleman RS. Kesicki EA. J. Am. Chem. Soc.  1994,  116:  11636 
  • 23 Adamczyk M. Akireddy SR. Mattingly PG. Reddy RE. Tetrahedron  2003,  59:  5749 
  • 24 Bew SP. Sweeney JB. Synlett  1991,  109