Skip to main content

Advertisement

SpringerLink
Log in

Diastereoselective synthesis of some carbocyclic 2′-oxa-3′-aza-nucleosides

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Two strategies for the synthesis of isoxazolidinyl nucleosides as potential antiviral agents are reported: a one-step approach based on 1,3-dipolar cycloaddition of D-lyxosyl nitrone with N,N-dibenzyl-9-vinyl adenine, and a two-step methodology based on the Vorbrüggen nucleosidation of the 5-acetoxyisoxazolidine. The chiral D-lyxosyl nitrone undergoes regioselective 1,3-dipolar cycloadditions with N,N-dibenzyl-9-vinyl adenine and vinyl acetate giving 5-substituted isoxazolidines as a mixture of four diastereoisomers in good yields. The condensation of 5-acetoxyisoxazolidine with silylated uracil, thymine, and N-acetylcytosine proceeded with moderate to good stereoselectivity with the formation of the expected isoxazolidinyl β-and α-nucleosides.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. P. Merino, Curr. Med. Chem. Anti-Infective Agents, 1, 389 (2002).

    Article  CAS  Google Scholar 

  2. U. Chiacchio, A. Corsaro, G. Gumina, A. Rescifina, D. Iannazzo, A. Piperno, G. Romeo, and R. Romeo, J. Org. Chem., 64, 9321 (1999).

    Article  CAS  Google Scholar 

  3. P. Merino, E. M. Del Alamo, F. Santiago, F. L. Merchan, A. Simon, and T. Tejero, Tetrahedron: Asymmetry, 11, 1543 (2000).

    Article  CAS  Google Scholar 

  4. U. Chiacchio, A. Corsaro, D. Iannazzo, A. Pieperno, A. Procopio, A. Rescifina, G. Romeo, R. Romeo, Eur. J. Org. Chem., 1893 (2001).

  5. U. Chiacchio, A. Corsaro, D. Iannazzo, A. Piperno, V. Pistara, A. Procopio, A. Rescifina, G. Romeo, R. Romeo, M. C. R. Siciliano, and E. Valveri, ARKIVOC, xi, 159 (2002).

    Google Scholar 

  6. E. Colacino, A. Converso, A. Ligueri, A. Napoli, C. Siciliano, and G. Sindona, Tetrahedron, 57, 8551 (2001).

    Article  CAS  Google Scholar 

  7. U. Chiacchio, A. Corsaro, D. Iannazzo, A. Piperno, V. Pistara, A. Rescifina, R. Romeo, V. Valveri, A. Mastino, and G. Romeo, J. Med. Chem., 46, 3696 (2003).

    Article  CAS  Google Scholar 

  8. R. Fischer, A. Drucková, L. Fišera, A. Rybár, C. Hametner, and M. K. Cyrañski, Synlett, 1113 (2002).

  9. R. Fischer, E. Hýrošová, A. Drucková, L. Fišera, C. Hametner, and M. K. Cyrañski, Synlett, 2364 (2003).

  10. J. Kubán, I. Blanáriková, L. Fišera, L. Jarošková, M. Fengler-Veith, V. Jäger, J. Kožíšek, O. Humpa, N. Prónayová, and V. Langer, Tetrahedron, 55, 9501 (1999).

    Article  Google Scholar 

  11. J. Kubán, A. Kolarovič, L. Fišera, V. Jäger, O. Humpa, and N. Prónayová, P. Ertl, Synlett, 1862 (2001).

  12. J. Kubán, A. Kolarovič, L. Fišera, V. Jäger, O. Humpa, and N. Prónayová, Synlett, 1862 (2001).

  13. I. Blanáriková-Hlobilová, Z. Kopaničáková, L. Fišera, M. K. Cyrañski, P. Salanski, J. Jurczak, and N. Prónayová, Tetrahedron, 59, 3333 (2003).

    Article  CAS  Google Scholar 

  14. B. Dugovič, T. Wiesenganger, L. Fišera, C. Hametner, and N. Prónayová, Heterocycles, 65, 591 (2005).

    Article  Google Scholar 

  15. B. Dugovič, L. Fišera, M. K. Cyranski, C. Hametner, N. Prónayová, and M. Obranec, Helvetica Chim. Acta, 88, 1432 (2005).

    Article  Google Scholar 

  16. A. Dondoni, S. Franco, F. Junquera, F. L. Merchan, P. Merino, and T. Tejero, Synth. Commun., 23, 2537 (1994).

    Google Scholar 

  17. P. Merino, S. Franco, F. L. Merchan, P. Romero, T. Tejero, and S. Uriel, Tetrahedron: Asymmetry, 14, 3731 (2003).

    Article  CAS  Google Scholar 

  18. R. Fischer, A. Drucková, L. Fišera, and C. Hametner, ARKIVOC, viii, 80 (2002).

    Google Scholar 

  19. H. Vorbrüggen, K. Krolikiewicz, and B. Bennua, Chem. Ber., 114, 1234 (1981).

    Google Scholar 

  20. P. Merino, S. Franco, F. L. Merchan, and T. Tejero, J. Org. Chem., 65, 5575 (2000).

    Article  CAS  Google Scholar 

  21. U. Chiacchio, A. Rescifina, A. Corsaro, V. Pistara, G. Romeo, and R. Romeo, Tetrahedron: Asymmetry, 11, 2045 (2000).

    Article  CAS  Google Scholar 

  22. U. Chiacchio, A. Corsaro, D. Iannazzo, A. Piperno, V. Pistara, A. Rescifina, R. Romeo, G. Sindona, and G. Romeo, Tetrahedron: Asymmetry, 14, 2717 (2003).

    Article  CAS  Google Scholar 

  23. U. Chiacchio, D. Iannazzo, A. Piperno, R. Romeo, G. Romeo, A. Rescifina, and M. Saglimbeni, Bioorg. Med. Chem., 14, 955 (2006).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology, 81237, Bratislava, Slovak Republic

    E. Hýrošová, L. Fišera, R. M.-A. Jame & M. Medveckíy

  2. Institute of Analytical Chemistry, Slovak University of Technology, 81237, Bratislava, Slovak Republic

    N. Prónayová

  3. Institute of Chemistry, Slovak Academy of Sciences, Bratislava, Slovak Republic

    M. Koóš

Authors
  1. E. Hýrošová
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. L. Fišera
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. R. M.-A. Jame
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. N. Prónayová
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. M. Medveckíy
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. M. Koóš
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Dedicated to Prof. Dr. E. Lukevics on the occasion of his 70th birthday

__________

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 01, pp. 14–21, Januvary, 2007.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Hýrošová, E., Fišera, L., Jame, R.MA. et al. Diastereoselective synthesis of some carbocyclic 2′-oxa-3′-aza-nucleosides. Chem Heterocycl Compd 43, 10–17 (2007). https://doi.org/10.1007/s10593-007-0002-4

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-007-0002-4

Keywords

Search

Navigation