Skip to main content
SpringerLink
Log in

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

  • Published:
Chemistry of Natural Compounds Aims and scope

Summary

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.

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

Literature cited

  1. F. R. Chalmers, H. T. Openshaw, and G. F. Smith, J. Chem. Soc., 1115 (1957).

  2. M. F. Millson and S. R. Robinson, J. Chem. Soc., 3362 (1955).

  3. M. M. Janot and J. L. Men, Compt. Rend.,240, 909 (1955).

    CAS  Google Scholar 

  4. J. A. Joule and G. F. Smith, J. Chem. Soc., 312 (1962).

  5. A. Hogman and A. J. Trey, Helv. Chim. Acta,40, 1866 (1957).

    Article  Google Scholar 

  6. M. Hanaoka, M. Hesse, and H. Schmid, Helv. Chim. Acta,53, 1723 (1970).

    Article  CAS  Google Scholar 

  7. H. Meisel and W. Döpke, Tetrahedron Lett.,17, 1285 (1971).

    Article  Google Scholar 

  8. J. L. Kaul, J. Trojanek, and A. K. Bose, Collection Czech. Chem. Commun.,35, 116 (1970).

    Article  CAS  Google Scholar 

  9. P. Kh. Yuldashev, J. L. Kaul, Z. Kablitsova, J. Trojanek, and S. Yu. Yunusov, Khim. Prirodn. Soedin.,2, 192 (1966).

    CAS  Google Scholar 

  10. A. Stoll and A. Hoffman, Helv. Chim. Acta,36, 1143 (1953).

    Article  CAS  Google Scholar 

  11. W. Mors, P. Zaltman, J. Beereboon, S. Pakzashi, and C. Djerassi, Chem. Ind. (London), 173 (1956).

  12. N. Peube-Locou, M. Koch, M. Plat, and P. Potier, Phytochemistry,11, 2109 (1972).

    Article  CAS  Google Scholar 

  13. S. Sakai, A. Kubo, and L. Haginiwa, Tetrahedron Lett., 1485 (1969).

  14. W. Klyne, R. J. Swan, N. J. Dastoor, A. A. Gorman, and H. Schmid, Helv. Chim. Acta,50, 115 (1967).

    Article  CAS  Google Scholar 

  15. K. Warnat, Helv. Chim. Acta,14, 997 (1931).

    Article  CAS  Google Scholar 

  16. R. A. Bell and J. K. Saunders, Can. J. Chem.,48, 1114 (1970).

    Article  CAS  Google Scholar 

  17. G. E. Bachers and T. Schaefer, Chem. Rev.,71, No. 6, 617 (1971).

    Article  CAS  Google Scholar 

  18. M. R. Yagudaev, V. M. Malikov, and S. Yu. Yunusov, Khim. Prirodn. Soedin.,9, 70 (1973).

    CAS  Google Scholar 

  19. P. J. Black, R. D. Brown, and M. L. Heffernan, Austr. J. Chem.,20, 1325 (1967).

    Article  CAS  Google Scholar 

Download references

Authors
  1. M. R. Yagudaev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. M. Malikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. S. Yu. Yunusov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 316–319, May–June, 1973.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Yagudaev, M.R., Malikov, V.M. & Yunusov, S.Y. 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. Chem Nat Compd 9, 302–304 (1973). https://doi.org/10.1007/BF00565686

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00565686

Keywords

Search

Navigation