Chemistry of Natural Compounds

, Volume 12, Issue 1, pp 55–59 | Cite as

Fragmentation of the macrocyclic ring of alkaloids with the otonecine nucleus

  • U. A. Abdullaev
  • Ya. V. Rashkev
  • S. Yu. Yunusov


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.


Alkaloid Macrocycle Pyrrolizidine Macrocyclic Ring Propionic Anhydride 


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Literature cited

  1. 1.
    Ya. V. Rashkev, U. A. Abdullaev, and S. Yu. Yunusov, Khim. Prirodn. Soedin., 40 (1974).Google Scholar
  2. 2.
    U. A. Abdullaev, Ya. V. Rashkev, and S. Yu. Yunusov, Khim. Prirodn. Soedin., 538 (1974).Google Scholar
  3. 3.
    N. I. Koretskaya, A. V. Danilova, and L. M. Utkin, Khim. Prirodn. Soedin., 22 (1965).Google Scholar
  4. 4.
    D. S. Khalilov and M. V. Telezhenetskaya, Khim Prirodn. Soedin., 685 (1973).Google Scholar
  5. 5.
    M. R. Cava, K. V. Rao, J. A. Weisbach, R. F. Raffauf, and B. Douglas, J. Org. Chem.,33, 3570 (1968).CrossRefGoogle Scholar
  6. 6.
    S. Kohlmunzer, H. Tomczyk, and A. Saint-Firmin, Dissert. Pharm. Pharmacol.,23, 419 (1971).Google Scholar
  7. 7.
    D. H. G. Crout, J. Chem. Soc., Perkin I, 1602 (1972).Google Scholar
  8. 8.
    K. B. Birnbaum, A. Klasek, P. Sedmera, G. Snatzke, L. F. Johnson, and F. Santavy, Tetrahedron Lett., 3421 (1971).Google Scholar
  9. 9.
    A. P. Orekhov, The Chemistry of Alkaloids of Plants of the USSR [in Russian] (1965), pp. 247, 248.Google Scholar
  10. 10.
    S. Yu. Yunusov and N. V. Plekhanova, Dokl. Akad. Nauk UzSSR, No. 4, 28 (1953).Google Scholar
  11. 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).Google Scholar

Copyright information

© Plenum Publishing Corporation 1977

Authors and Affiliations

  • U. A. Abdullaev
  • Ya. V. Rashkev
  • S. Yu. Yunusov

There are no affiliations available

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