C14-Labeled Cardiac Glycosides

  • Georg Rabitzsch


An essential structural and pharmacological characteristic of cardenolides is an a, ß-unsaturated γ-lactone ring (the butenolide ring) in the 17 β-position. Ruzicka, Reichstein, and Fürst [1] and others [2–5] first demonstrated the possibility of its synthesis from steroids other than cardenolides by means of the Reformatsky reaction [6,7]. By reaction of various 21-acyloxypregnanone-(20) derivatives with bromacetic acid ethyl ester and zinc, they obtained the hydroxylactone after acid cleavage of the organozinc compound and the corresponding ∆ 20,22-steroid lactone after subsequent dehydration. These studies were performed only with 14-deoxy derivatives because of the relatively strong nature of the reactions, but in 1947 Plattner and coworkers [8] achieved partial synthesis of a 14 β-OH compound for the first time. However, the yields were at most 20%, as was also the case for the partial synthesis of digitoxigenin-3-acetate-23-C14 later described by Turba and Scholtissek [9], probably because the lability of the 14 β -OH compounds is higher than usual for the Reformatsky reaction.


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  1. 1.
    Ruzicka, L., Reichstein, T., and Fürst, A., Helv. Chim. Acta 24: 76 (1941).CrossRefGoogle Scholar
  2. 2.
    Fried, J., Linville, R.G., and Elderfield, R. C., J. Org. Chem. 7: 362 (1942).CrossRefGoogle Scholar
  3. 3.
    Ruzicka, L., Plattner, P.A., and Balla, G., Helv. Chim. Acta 25: 65 (1942);CrossRefGoogle Scholar
  4. 4.
    Plattner, P.A., Ruzicka, L., and Fürst, A., Helv. Chim. Acta 26: 2274 (1943).CrossRefGoogle Scholar
  5. 5.
    Ruzicka, L., Plattner, P.A., and Pataki, J., Helv. Chim. Acta 27: 988 (1944).CrossRefGoogle Scholar
  6. 6.
    Reformatsky, S., Chem. Ber. 20: 1210 (1887).CrossRefGoogle Scholar
  7. 7.
    Shriner, R. L., Org. Reactions 1: 1 (1942).Google Scholar
  8. 8.
    Plattner, P.A., Ruzicka, L., Heusser, H., and Angliker, E., Helv. Chim. Acta 30: 1073 (1947).CrossRefPubMedGoogle Scholar
  9. 9.
    Turba, F., and Scholtissek, Ch., Z. Physiol. Chem. 296: 87 (1954).CrossRefGoogle Scholar
  10. 10.
    Ceiling, E. M. K., Kelsey, F.E., McIntosh, B. J., and Ganz, A., Science 108: 558 (1948).CrossRefGoogle Scholar
  11. 11.
    Okita, G.T., Kelsey, F.E., Walaszek, E. J., and Geiling,E.M.K., J. Pharmacol. Exp. Therap. 110: 244 (1954).Google Scholar
  12. 12.
    Rabitzsch, G., Second International Symposium on the Chemistry of Natural Products, Prague (August 27 to September 2, 1962 ).Google Scholar
  13. 13.
    Rabitzsch, G., Monatsber. Deut. Akad. Wiss. Berlin 5: 299 (1963).Google Scholar
  14. 14.
    Viehe, H.G., and Reinstein, M., Chem. Ber. 95: 2557 (1962).CrossRefGoogle Scholar
  15. 15.
    Straub, W., Biochem. Z. 28: 392 (1910).Google Scholar
  16. 16.
    Rabitzsch, G., International Conference on Medicinal Plant Research, Sofia (September 16–18, 1963 ).Google Scholar
  17. 17.
    Rabitzsch, G., Naturwissenschaften 50: 225 (1963).CrossRefGoogle Scholar

Copyright information

© New England Nuclear Corporation 1966

Authors and Affiliations

  • Georg Rabitzsch
    • 1
  1. 1.Institute for Circulation ResearchGerman Academy of SciencesBerlin-BuchGermany

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