Skip to main content
SpringerLink
Log in

Beweis des Steringerüstes von Ouabagenin

  • Kurze Mitteilungen
  • Published:
Experientia Aims and scope Submit manuscript

Summary

Ouabagenin (I) has been degraded stepwise to the known 3-methoxy-17β-carbomethoxy-△1,3,5:10-estratriene (XII). Thus the presence of a normal steroid skeleton and the β-configuration of the butenolidering at C-17 is proven. The 14β-configuration of the hydroxyl at C-14 was also proven. As a result of these and earlier findings, structure I can be definitely assigned to ouabagenin.

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

References

  1. C. Mannich undG. Siewert, Bert. dtsch. chem. Ges.75, 737 (1942).

    Article  Google Scholar 

  2. W. A. Jacobs undN. M. Bigelow, J. biol. Chem.96, 647 (1932).

    Article  CAS  Google Scholar 

  3. A. Meyrat undT. Reichstein, Helv. chim. Acta31, 2104 (1948).

    Article  PubMed  CAS  Google Scholar 

  4. R. F. Raffauf undT. Reichstein, Helv. chim. Acta31, 2111 (1948).

    Article  PubMed  CAS  Google Scholar 

  5. W. A. Jacobs undN. M. Bigelow, J. biol. Chem.96, 647 (1932);101, 15 (1933).

    Article  CAS  Google Scholar 

  6. A. Meyrat undT. Reichstein, Helv. chim. Acta31, 2104 (1948).

    Article  PubMed  CAS  Google Scholar 

  7. K. Florey undM. Ehrenstein, J. org. Chem.19, 1174 (1954).

    Article  CAS  Google Scholar 

  8. B. P. A. Sneeden undR. B. Turner, J. Amer. Chem. Soc.77, 130 (1955).

    Article  CAS  Google Scholar 

  9. Ch. Tamm, Helv. chim. Acta38, 147 (1955).

    Article  CAS  Google Scholar 

  10. R. Tschesche undG. Snatzke, Chem. Ber.88, 1558 (1955).

    Article  CAS  Google Scholar 

  11. R. B. Turner undJ. A. Meschino, J. Amer. chem. Soc.78, 5130 (1956).

    Article  CAS  Google Scholar 

  12. C. Mannich undG. Siewert, Ber. dtsch. chem. Ges.75, 737 (1942).

    Article  Google Scholar 

  13. R. P. A. Sneeden undR. B. Turner, J. Amer. chem. Soc.75, 3510 (1953).

    Article  CAS  Google Scholar 

  14. Ch. Tamm, Helv. chim. Acta38, 147 (1955).

    Article  CAS  Google Scholar 

  15. G. I. Poos, G. E. Arth, R. E. Beyler undL. H. Sarett, J. Amer. chem. Soc.75, 422 (1953).

    Article  CAS  Google Scholar 

  16. A. Arnaud, C. r. Acad. Sci.106, 1011 (1888).

    Google Scholar 

  17. W. A. Jacobs undN. M. Bigelow, J. biol. Chem.96, 647 (1932);101, 15 (1933).

    Article  CAS  Google Scholar 

  18. C. Mannich undG. Siewert, Ber. dtsch. chem. Ges.75, 737 (1942).

    Article  Google Scholar 

  19. R. P. A. Sneeden undR. B. Turner, J. Amer. chem. Soc.75, 3510 (1953).

    Article  CAS  Google Scholar 

  20. Ch. Tamm, Helv. chim. Acta38, 147 (1955).

    Article  CAS  Google Scholar 

  21. C. Mannich undG. Siewert, Ber. dtsch. chem. Ges.75, 737 (1942).

    Article  Google Scholar 

  22. R. P. A. Sneeden undR. B. Turner, J. Amer. chem. Soc.75, 3510 (1953).

    Article  CAS  Google Scholar 

  23. Ch. Tamm, Helv. chim. Acta38, 147 (1955).

    Article  CAS  Google Scholar 

  24. R. P. A. Sneeden undR. B. Turner, J. Amer. chem. Soc.75, 3510 (1953).

    Article  CAS  Google Scholar 

  25. C. Djerassi undR. Ehrlich, J. org. Chem.19, 1353 (1954).

    Article  Google Scholar 

  26. C. Djerassi undC. R. Scholz, J. Amer. chem. Soc.71, 3962 (1949).

    Article  CAS  Google Scholar 

  27. G. M. Barton, R. S. Evans undJ. A. F. Gardner, Nature170, 249 (1952).

    Article  CAS  Google Scholar 

  28. R. Kuhn undH. J. Haas, Angew. Chemie67, 785 (1955).

    Google Scholar 

  29. C. Djerassi undC. R. Scholz, J. Amer. chem. Soc.71, 3962 (1949).

    Article  CAS  Google Scholar 

  30. Wir danken Herrn Prof.C. Djerassi bestens für die Überlassung einer Probe von authentischem 3-Methoxy-17β-carboxyöstra-trien-(1,3,5:10).

Download references

Author information

Authors and Affiliations

  1. Organisch-chemische Anstalt der Universität Basel, Switzerland

    Ch. Tamm, G. Volpp & G. Baumgartner

Authors
  1. Ch. Tamm
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. G. Volpp
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. G. Baumgartner
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Glykoside und Aglykone, 178. Mitteilung.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Tamm, C., Volpp, G. & Baumgartner, G. Beweis des Steringerüstes von Ouabagenin. Experientia 13, 185–187 (1957). https://doi.org/10.1007/BF02157151

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02157151

Search

Navigation