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Chemistry of Natural Compounds

, Volume 6, Issue 2, pp 228–231 | Cite as

A study of the stereochemistry of alkaloids of the galanthamine type by NMR spectroscopy. I

  • M. R. Yagudaev
  • A. Abdusamatov
  • S. Yu. Yunusov
Article
  • 32 Downloads

Conclusions

  1. 1.

    From a consideration of the spin-spin coupling constants of the protons in the NMR spectra of galanthamine, epigalanthamine, and their acetyl derivatives, is has been established that the OH group in galanthamine is quasi-axial and in epigalanthamine it is quasi-equatorial, and ring B has the half-chair conformation in cis fusion with ring C.

     
  2. 2.

    The axial proton at C1 in epigalanthamine gives a signal in a weaker field than the corresponding equatorial proton in galanthamine. The dependence of the chemical shift of the signal of the OH proton in galanthamine on the concentration and the temperature show the existence of an intermolecular hydrogen bond betwen the molecules of the substance in solutions.

     

Keywords

Hydrogen Hydrogen Bond Organic Chemistry Chemical Shift Alkaloid 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    D. H. R. Barton and G. W. Kirby J. Chem. Soc., 806, 1962.Google Scholar
  2. 2.
    H. Mishima, M. Kurabayashi and I. Iwai, J. Org. Chem., 88, 262, 1963.Google Scholar
  3. 3.
    H. P. Volpp and L. Bubewa-Iwanowa. Chem. Ber., 97, 563, 1964.Google Scholar
  4. 4.
    D. J. Williams and D. Rogers, Proc. Chem. Soc., 357, 1964.Google Scholar
  5. 5.
    L. M. Jackman, Appl. of NMR Spectroscopy in Org. Chem., New York-London, 1959.Google Scholar
  6. 6.
    N. Bhacca and D. Wi liams, Applications of NMR Spectroscopy in Organic Chemistry [Russian translation], Moscow, 1966.Google Scholar
  7. 7.
    C. E. Johnson and F. A. Bovey, J. Chem. Phys., 29, 1012, 1958.Google Scholar
  8. 8.
    E. W. Garbisch, J. Am. Chem. Soc., 86, 5561, 1964.Google Scholar
  9. 9.
    Yu. Yu. Samitov, Author's abstract of doctoral dissertation [in Russian], Kazan, 1967.Google Scholar
  10. 10.
    J. C. W. Ma and E. W. Warnhoff, Canad. J. Chem., 43, 1849, 1965.Google Scholar

Copyright information

© Consultants Bureau 1973

Authors and Affiliations

  • M. R. Yagudaev
    • 1
  • A. Abdusamatov
    • 1
  • S. Yu. Yunusov
    • 1
  1. 1.Institute of the Chemistry of Plant SubstancesASUzSSR

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