Skip to main content
SpringerLink
Log in

Synthetic studies towards (±)-aristeromycin and its 5′-homo-analogue

Synthesestudien zu (±)-Aristeromycin und seinem 5′-homo-Analogon

  • Organische Chemie Und Biochemie
  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Summary

A new synthetic pathway to the carbocyclic nucleoside analogues (±)-aristeromycin (15) and its 5′-homo-derivative (17) has been developed starting form norborn-5-en-2-one using nucleophilic substitution of a sulfonate ester group by the aglycone.

Zusammenfassung

Ausgehend von Norborn-5-en-2-on wurden neue Synthesewege für (±)-Aristeromycin (15) und sein 5′-homo-Analogon (17) entwickelt, wobei die Einführung der Base durchS N2-Austausch einer Sulfonsäureestergruppe erfolgt.

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. For an overview see: a) Marquez VE, Lim M-I (1986) Med Res Rev6: 1;

    Google Scholar 

  2. Borthwick AD, Biggadike K (1992) Tetrahedron48: 571;

    Google Scholar 

  3. Agrofoglio L, Suhas E, Farese A, Condom R, Challand SR, Earl RA, Guedj R (1994) Tetrahedron50: 10611

    Google Scholar 

  4. Shealy YF, Clayton JD (1966) J Am Chem Soc88: 3885;

    Google Scholar 

  5. Shealy YF, Clayton JD (1969) J Am Chem Soc91: 3075

    Google Scholar 

  6. Kusaka T, Yamamoto H, Shibata M, Muroi M, Kishi T, Mizuno K (1968) J Antibiotics21: 255

    Google Scholar 

  7. Robins RK, Revankar GR (1988) In: DeClercq E, Walker RT (eds) Antiviral Drug Development. Plenum, New York, p 11

    Google Scholar 

  8. MacCoss M, Robins MJ (1990) In: Wilman DEV (ed) Chemistry of Antitumor Agents. Blackie & Son, U.K., p 261;

    Google Scholar 

  9. Robins RK, Kini GD (1990) ibid, In:, p 299

    Google Scholar 

  10. Saksena AK (1980) Tetrahedron Lett21: 133;

    Google Scholar 

  11. Cermak RC, Vince R (1981) Tetrahedron Lett22: 2331;

    Google Scholar 

  12. Katagiri N, Watanabe N, Kaneko C (1990) Chem Pharm Bull38: 69;

    Google Scholar 

  13. Tanaka M, Yoshioka M, Sakai K (1992) J Chem Soc Chem Commun: 1454

  14. Madhavan GVB, Martin JC (1986) J Org Chem51: 1287;

    Google Scholar 

  15. Trost BM, Kuo G-H, Benneche T (1988) J Am Chem Soc110: 621

    Google Scholar 

  16. Arita M, Adachi K, Ito Y, Sawai H, Ohno M (1983) J Am Chem Soc105: 4049;

    Google Scholar 

  17. Tadano K, Hoshino M, Ogawa S, Suami T (1988) J Org Chem53: 1427;

    Google Scholar 

  18. Arai Y, Hayashi Y, Yamamoto M, Takayema H, Koizumi T (1988) J Chem Soc Perkin Trans1, 3133;

    Google Scholar 

  19. Wolfe MS, Borcherding DR, Borchardt RT (1989) Tetrahedron Lett30: 1453;

    Google Scholar 

  20. Yoshikawa M, Okaichi Y, Cha BC, Kitagawa I (1990) Tetrahedron46: 7459;

    Google Scholar 

  21. Trost BM, Li L, Guille S (1992) J Am Chem Soc114: 8745

    Google Scholar 

  22. Jones MF, Roberts SM (1988) J Chem Soc Perkin Trans1, 2927

    Google Scholar 

  23. Eichberger G, Penn G, Faber K, Griengl H (1986) Tetrahedron Lett27: 2843

    Google Scholar 

  24. Marschner C, Penn G, Griengl H (1990) Tetrahedron Lett31: 2873;

    Google Scholar 

  25. Marschner C, Baumgartner J, Griengl H (1995) J Org Chem60: 5224

    Google Scholar 

  26. Mancuso AJ, Huang S-L, Swern D (1978) J Org Chem43: 165

    Google Scholar 

  27. Baumgartner H, Marschner C, Pucher R, Griengl H (1991) Tetrahedron Lett32: 611

    Google Scholar 

  28. Ötvös L, Béres J, Ságy G, Tömösközi I, Gruber L (1987) Tetrahedron Lett28: 6381;

    Google Scholar 

  29. Béres J, Ságy G, Tömösközi I, Gruber L, Gulácsi E, Ötvös L (1988) Tetrahedron Lett29: 2681

    Google Scholar 

  30. Greene TW, Wuts PGM (1991) Protective Groups in Organic Synthesis, 2nd edn. Wiley, New York

    Google Scholar 

  31. Wolfe MS, Anderson BL, Borcherding DR, Borchardt RT (1990) J Org Chem55: 4712

    Google Scholar 

  32. Pausacker KH (1953) J Chem Soc107: 514

    Google Scholar 

  33. For detailed information see: Balzarini J, Baumgartner H, Bodenteich M, De Clercq E, Griengl H (1989) Nucleosides & Nucleotides8: 855

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Organic Chemistry, Technical University Graz, A-8010, Graz, Austria

    H. Kapeller, H. Baumgartner & H. Griengl

Authors
  1. H. Kapeller
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. H. Baumgartner
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. H. Griengl
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kapeller, H., Baumgartner, H. & Griengl, H. Synthetic studies towards (±)-aristeromycin and its 5′-homo-analogue. Monatsh Chem 128, 191–200 (1997). https://doi.org/10.1007/BF00807308

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00807308

Keywords

Search

Navigation