Chemistry of Natural Compounds

, Volume 9, Issue 3, pp 302–304 | Cite as

The use of the intramolecular nuclear Overhauser effect to establish the positions of substituents in the aromatic nuclei of the alkaloids majoridine and O-acetyl-N-methyllochnerine

  • M. R. Yagudaev
  • V. M. Malikov
  • S. Yu. Yunusov


The use of the NOE method has permitted the unambiguous determination of the position of the OCH3 groups at C10 in the aromatic nuclei of majoridine and of O-acetyl-N-methyllochnerine and has thereby shown the possibility of using this method for determining the position of substituents in the benzene rings of the N-methylindoline and indole alkaloids.


Alkaloid Indole Aromatic Proton Indole Alkaloid Indoline 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    F. R. Chalmers, H. T. Openshaw, and G. F. Smith, J. Chem. Soc., 1115 (1957).Google Scholar
  2. 2.
    M. F. Millson and S. R. Robinson, J. Chem. Soc., 3362 (1955).Google Scholar
  3. 3.
    M. M. Janot and J. L. Men, Compt. Rend.,240, 909 (1955).Google Scholar
  4. 4.
    J. A. Joule and G. F. Smith, J. Chem. Soc., 312 (1962).Google Scholar
  5. 5.
    A. Hogman and A. J. Trey, Helv. Chim. Acta,40, 1866 (1957).CrossRefGoogle Scholar
  6. 6.
    M. Hanaoka, M. Hesse, and H. Schmid, Helv. Chim. Acta,53, 1723 (1970).CrossRefGoogle Scholar
  7. 7.
    H. Meisel and W. Döpke, Tetrahedron Lett.,17, 1285 (1971).CrossRefGoogle Scholar
  8. 8.
    J. L. Kaul, J. Trojanek, and A. K. Bose, Collection Czech. Chem. Commun.,35, 116 (1970).CrossRefGoogle Scholar
  9. 9.
    P. Kh. Yuldashev, J. L. Kaul, Z. Kablitsova, J. Trojanek, and S. Yu. Yunusov, Khim. Prirodn. Soedin.,2, 192 (1966).Google Scholar
  10. 10.
    A. Stoll and A. Hoffman, Helv. Chim. Acta,36, 1143 (1953).CrossRefGoogle Scholar
  11. 11.
    W. Mors, P. Zaltman, J. Beereboon, S. Pakzashi, and C. Djerassi, Chem. Ind. (London), 173 (1956).Google Scholar
  12. 12.
    N. Peube-Locou, M. Koch, M. Plat, and P. Potier, Phytochemistry,11, 2109 (1972).CrossRefGoogle Scholar
  13. 13.
    S. Sakai, A. Kubo, and L. Haginiwa, Tetrahedron Lett., 1485 (1969).Google Scholar
  14. 14.
    W. Klyne, R. J. Swan, N. J. Dastoor, A. A. Gorman, and H. Schmid, Helv. Chim. Acta,50, 115 (1967).CrossRefGoogle Scholar
  15. 15.
    K. Warnat, Helv. Chim. Acta,14, 997 (1931).CrossRefGoogle Scholar
  16. 16.
    R. A. Bell and J. K. Saunders, Can. J. Chem.,48, 1114 (1970).CrossRefGoogle Scholar
  17. 17.
    G. E. Bachers and T. Schaefer, Chem. Rev.,71, No. 6, 617 (1971).CrossRefGoogle Scholar
  18. 18.
    M. R. Yagudaev, V. M. Malikov, and S. Yu. Yunusov, Khim. Prirodn. Soedin.,9, 70 (1973).Google Scholar
  19. 19.
    P. J. Black, R. D. Brown, and M. L. Heffernan, Austr. J. Chem.,20, 1325 (1967).CrossRefGoogle Scholar

Copyright information

© Plenum Publishing Corporation 1975

Authors and Affiliations

  • M. R. Yagudaev
  • V. M. Malikov
  • S. Yu. Yunusov

There are no affiliations available

Personalised recommendations