Skip to main content
SpringerLink
Log in

Fragmentation of the macrocyclic ring of alkaloids with the otonecine nucleus

  • Published:
Chemistry of Natural Compounds Aims and scope

Summary

It has been shown that the fragmentation of the macrocycle of the otonecine bases qualitatively resembles the decomposition of macrocyclic alkaloids with the retronecine skeleton. The presence of an oxygen-containing substituent at C5′ and of an alkoxy group at C2′, when there is no C5′=C6′ double bond, substantially changes the direction of decomposition of the macrocycle.

A similarity of the spectra of 11- and 12-membered bases with similar mutual orientation of CH3 groups at C2′ and C3′ has been noted.

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. Ya. V. Rashkev, U. A. Abdullaev, and S. Yu. Yunusov, Khim. Prirodn. Soedin., 40 (1974).

  2. U. A. Abdullaev, Ya. V. Rashkev, and S. Yu. Yunusov, Khim. Prirodn. Soedin., 538 (1974).

  3. N. I. Koretskaya, A. V. Danilova, and L. M. Utkin, Khim. Prirodn. Soedin., 22 (1965).

  4. D. S. Khalilov and M. V. Telezhenetskaya, Khim Prirodn. Soedin., 685 (1973).

  5. M. R. Cava, K. V. Rao, J. A. Weisbach, R. F. Raffauf, and B. Douglas, J. Org. Chem.,33, 3570 (1968).

    Article  CAS  Google Scholar 

  6. S. Kohlmunzer, H. Tomczyk, and A. Saint-Firmin, Dissert. Pharm. Pharmacol.,23, 419 (1971).

    Google Scholar 

  7. D. H. G. Crout, J. Chem. Soc., Perkin I, 1602 (1972).

  8. K. B. Birnbaum, A. Klasek, P. Sedmera, G. Snatzke, L. F. Johnson, and F. Santavy, Tetrahedron Lett., 3421 (1971).

  9. A. P. Orekhov, The Chemistry of Alkaloids of Plants of the USSR [in Russian] (1965), pp. 247, 248.

  10. S. Yu. Yunusov and N. V. Plekhanova, Dokl. Akad. Nauk UzSSR, No. 4, 28 (1953).

  11. C. C. J. Culvenor, D. H. G. Crout, W. Klyne, W. P. Mose, J. D. Renwik, and P. M. Scopes, J. Chem. Soc. (c), 3653 (1971).

Download references

Authors
  1. U. A. Abdullaev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ya. V. Rashkev
    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, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 66–71, January–February, 1976.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Abdullaev, U.A., Rashkev, Y.V. & Yunusov, S.Y. Fragmentation of the macrocyclic ring of alkaloids with the otonecine nucleus. Chem Nat Compd 12, 55–59 (1976). https://doi.org/10.1007/BF00570183

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00570183

Keywords

Search

Navigation