Synthesis 2010(3): 425-430  
DOI: 10.1055/s-0029-1217142
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Synthesis of Novel Isonucleoside Analogues of Purine with a Tetrahydropyran Ring

Laura Estévez, Pedro Besada, Yagamare Fall, Marta Teijeira, Carmen Terán*
Departamento de Química Orgánica, Facultad de Química, Universidad de Vigo, 36310 Vigo, Spain
Fax: +34(986)812262; e-Mail: mcteran@uvigo.es;
Further Information

Publication History

Received 24 July 2009
Publication Date:
24 November 2009 (online)

Abstract

New tetrahydropyran isonucleoside derivatives of purine, with cis or trans configuration, were stereoselectively synthesized in moderate yield by a convergent strategy based on Mitsunobu coupling. The key starting material was a bicyclic lactone.

    References

  • 1a Cheson DK. Keating MJ. Plunkett W. Nucleoside Analogs in Cancer Therapy   Marcel Dekker; New York: 1997. 
  • 1b Chu CK. Recent Advances in Nucleosides: Chemistry and Biological Properties   Gordon and Breach Science Publishers; Amsterdam: 2001. 
  • 2 Simons C. Nucleoside Mimetics: Their Chemistry and Biological Properties   Gordon and Breach Science Publishers; Amsterdam: 2001. 
  • 3 Cookson RC. Dudfield PJ. Newton RF. Ravenscroft P. Scopes DIC. Cameron JM. Eur. J. Med. Chem.  1985,  20:  375 
  • 4 Nair V. Antiviral Isonucleosides: Discovery, Chemistry and Chemical Biology, In Recent Advances in Nucleosides: Chemistry and Chemotherapy   Chu CK. Elsevier Science; Amsterdam: 2002. 
  • 5 Nair V. St. Clair M. Rearson JE. Krasny HC. Hazen RJ. Paff MT. Boone LR. Tisdale M. Nájera I. Dornsife RE. Averett DR. Borroto-Esoda K. Yale JL. Zimmerman TP. Rideout JL. Antimicrob. Agents Chemother.  1995,  39:  1993 
  • 6a Nair V. Chun B.-K. Vadakkan JJ. Tetrahedron  2004,  60:  10261 
  • 6b Nair V. Piotrowska DG. Okello M. Vadakkan J. Nucleosides, Nucleotides Nucleic Acids  2007,  26:  687 
  • 7 Nair V. Jahnke TS. Antimicrob. Agents Chemother.  1995,  39:  1017 
  • 8 Mansour TK. Storer R. Curr. Pharm. Des.  1997,  3:  227 
  • 9a Chun B.-K. Wang P. Hassan A. Du J. Tharnish PM. Murakami E. Stuyver L. Otto MJ. Schinazi RF. Watanabe KA. Nucleosides, Nucleotides Nucleic Acids  2007,  26:  83 
  • 9b Chun B.-K. Vadakkan JJ. Nair V. Nucleosides, Nucleotides Nucleic Acids  2005,  24:  725 
  • 9c Jiang C. Li B. Guan Z. Yang Z. Zhanga L. Zhanga L. Bioorg. Med. Chem.  2007,  15:  3019 
  • 10a Bouiset T. Gosselin G. Griffe L. Meillon J.-C. Storer R. Tetrahedron  2008,  64:  6657 
  • 10b Sanki AK. Bhattacharya R. Atta AK. Suresh ChG. Pathak T. Tetrahedron  2008,  64:  10406 
  • 10c Yoshimura Y. Asami K. Matsui H. Tanaka H. Takahata H. Org. Lett.  2006,  8:  6015 
  • 10d Wang F. Yang Z.-J. Jin H.-W. Zhang L.-R. Zhang L.-H. Tetrahedron: Asymmetry  2007,  18:  2139 
  • 11 Estrada E. Uriarte E. Montero A. Teijeira M. Santana L. De Clercq E. J. Med. Chem.  2000,  43:  1975 
  • 12 Viña D. Santana L. Uriarte E. Terán C. Tetrahedron  2005,  61:  473 
  • 13 González-Moa MJ. Besada P. Terán C. Synthesis  2006,  3973 
  • 14 Canoa P. González-Moa MJ. Teijeira M. Terán C. Uriarte E. Pannecouque C. De Clercq E. Chem. Pharm. Bull.  2006,  54:  1418 
  • 15 Alonso D. Pérez M. Gómez G. Covelo B. Fall Y. Tetrahedron  2005,  61:  2021 
  • 16 Limoro T. Ohtsuka Y. Oishi T. Tetrahedron Lett.  1991,  32:  1209