Chemistry of Natural Compounds

, Volume 25, Issue 1, pp 1–13 | Cite as

Dimeric quinoline alkaloids

  • I. A. Bessonova
  • S. Yu. Yunusov


The review is denoted to an analysis of the literature on the investigation of dimeric quinoline alkaloids, which are divided into four groups depending on the structures of the terpenoid moiety. The natural sources, structures, stereochemical features, possible biogenetic schemes of formation, and methods of synthesizing the alkaloids of this group are considered.


Organic Chemistry Alkaloid Quinoline Natural Source Terpenoid 
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.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    J. Reisch, I. Mester, J. Korosi, and K. Szendrei, Tetrahedron Lett., 3681 (1978).Google Scholar
  2. 2.
    H. Furukawa, T.-S. Wu, C.-S. Kuoh, T. Sato, Y. Nagai, and K. Kagei, Chem. Pharm. Bull.,32, 1647 (1984).Google Scholar
  3. 3.
    J. P. Kutney, T. Inaba, and D. L. Dreyer, Tetrahedron,26, 3171 (1970).Google Scholar
  4. 4.
    G. B. Guise, E. Ritchie, G. G. Senior, and W. C. Taylor, Aust. J. Chem.,20, 2429 (1967).Google Scholar
  5. 5.
    D. R. Chakraborty, S. Roy, A. Chakraborty, A. K. Mandal, and B. K. Chowdhury, Tetrahedron,36, 3563 (1980).Google Scholar
  6. 6.
    G. S. R. Subba Rao, B. Ravindranath, and V. P. Sashi Kumar, Phytochemistry,23, 399 (1984).Google Scholar
  7. 7.
    Y.-C. Kong, K.-F. Cheng, R. C. Cambie, and P. G. Waterman, J. Chem. Soc., Chem. Commun., 47 (1985).Google Scholar
  8. 8.
    M. A. Caolo and F. R. Stermitz, Tetrahedron,35, 1487 (1979).Google Scholar
  9. 9.
    M. F. Grunden, The Alkaloids; Specialist Periodical Reports, The Chemical Society, London, Vol. 13, (1983), p. 116.Google Scholar
  10. 10.
    M. F. Grundon, Natural Product Reports, The Chemical Society, London, Vol. 1 (1984), p. 195; Vol. 2 (1985), p. 393; Vol. 4 (1987), p. 225.Google Scholar
  11. 11.
    L. Yard and R. Y. Wong, Aust. J. Chem.,34, 1625 (1981).Google Scholar
  12. 12.
    I. Mester, J. Reisch, K. Szendrei, and J. Korosi, Ann. Chem., 1785 (1979).Google Scholar
  13. 13.
    A. W. Sangster and K. L. Stuart, Chem. Rev.,65, 69 (1965).Google Scholar
  14. 14.
    H. Rapoport and K. G. Holden, J. Am. Chem. Soc.,82, 4392 (1960).Google Scholar
  15. 15.
    S. Goodwin, J. N. Schoolery, and L. F. Johnston, J. Am. Chem. Soc.,81, 3065 (1959).Google Scholar
  16. 16.
    J. Vaquette, M. S. Hifnawy, J. L. Pousset, A. Fournet, A. Bouquet, and A. Cave, Phytochemistry,15, 743 (1976).Google Scholar
  17. 17.
    T. Higa and P. J. Sheuer, Phytochemistry,13, 1269 (1974).Google Scholar
  18. 18.
    J. Reisch, J. Korosi, K. Szendrei, I. Novak, and E. Minker, Phytochemistry,14, 1678 (1975).Google Scholar
  19. 19.
    J. Jurd and M. Benson, J. Chem. Soc. Chem. Commun., 92 (1983).Google Scholar
  20. 20.
    J. Jurd, M. Benson, and R. Y. Wong, Aust. J. Chem.,36, 759 (1983).Google Scholar
  21. 21.
    T. B. Ngadjui, J. F. Ayafor, B. L. Sondengam, J. D. Connolly, D. S. Rycroft, S. A. Khalid, P. G. Waterman, N. M. Brown, M. F. Grundon, and V. N. Ramachandran, Tetrahedron Lett.,23, 2041 (1982).Google Scholar
  22. 22.
    L. Jurd, R. Y. Wong, and M. Benson, Aust. J. Chem.,35, 2505 (1982).Google Scholar
  23. 23.
    J. F. Ayafor, B. L. Sondengam, and B. Ngadjui, Tetrahedron Lett.,21, 3293 (1980).Google Scholar
  24. 24.
    S. A. Khalid and P. G. Waterman, Phytochemistry,20, 2761 (1981).Google Scholar
  25. 25.
    N. S. Bhacca and D. H. Williams, Applications of NMR Spectroscopy in Organic Chemistry, Holden-Day, San Francisco, (1964) [Russian translation, Moscow (1966), p. 150].Google Scholar
  26. 26.
    N. M. D. Brown, M. F. Gundron, D. M. Harrison, and S. A. Surgenor, Tetrahedron,36, 3579 (1980).Google Scholar
  27. 27.
    M. Barfield, J. Am. Chem. Soc.,93, 1066 (1971).Google Scholar
  28. 28.
    C. S. Barnes, M. I. Strong, and J. L. Occolowitz, Tetrahedron,19, 839 (1963).Google Scholar
  29. 29.
    M. A. Caolo, O. P. Anderson, and F. R. Stermitz, Tetrahedron,35, 1493 (1979).Google Scholar
  30. 30.
    S. Mitaku, A.-L. Skaltsounis, F. Tillequin, M. Koch, J. Pusset, and G. Chauviere, J. Nat. Prod.,48, 772 (1985).Google Scholar
  31. 31.
    R. F. C. Brown, J. J. Hobbs, G. K. Hughes, and E. Ritchie, Aust. J. Chem.,7, 348 (1954).Google Scholar
  32. 32.
    V. I. Akmedzhanova, I. A. Bessanova, and S. Yu. Yunusov, Khim. Prir. Soedin., 262 (1974).Google Scholar
  33. 33.
    B. Tashkhodzhaev, S. V. Lindeman, I. A. Bessonova, D. M. Razakova, E. N. Tsapkina, and Yu. T. Struchko, Khim. Prir. Soedin., 838 (1988).Google Scholar
  34. 34.
    D. M. Clugston and D. B. McLean, Can. J. Chem.,43, 2516 (1965).Google Scholar
  35. 35.
    C. S. Barnes and J. L. Occolowitz, Aust. J. Chem.,17, 975 (1964).Google Scholar
  36. 36.
    M. F. Grundon, D. M. Harrison, and C. G. Spyropoulos, J. Chem. Soc. Chem. Commun., 51 (1974).Google Scholar
  37. 37.
    M. F. Grundon, D. M. Harrison, and C. G. Spyropoulos, J. Chem. Soc. Chem. Commun., 302 (1975).Google Scholar
  38. 38.
    R. M. Bowman, M. F. Grundon, and K. F. Jamos, J. Chem. Soc. Perkin I., 1055 (1973).Google Scholar
  39. 39.
    M. F. Grundon, V. N. Ramachandran, and B. M. Sloan, Tetrahedron Lett.,22, 3105 (1981).Google Scholar
  40. 40.
    D. R. Schroeder and F. R. Stermitz, Tetrahedron,19, 4309 (1985).Google Scholar
  41. 41.
    S. Wawzonek, in: Heterocyclic Compounds, ed. R. C. Elderfield, Wiley, New York, Vol. 2 (1951) [Russian translation, IL, Moscow (1954), p. 315].Google Scholar
  42. 42.
    J. F. Ayufor, B. L. Sondengam, J. D. Connolly, and D. S. Rycroft, Tetrahedron Lett.,26, 4529 (1985).Google Scholar
  43. 43.
    M. Ramesh, P. S. Mohan, and P. Shanmugam, Tetrahedron,40, 4041 (1984).Google Scholar
  44. 44.
    M. F. Grundon and M. J. Rutherford, J. Chem. Soc. Perkin I., 197 (1985).Google Scholar
  45. 45.
    J. Reisch, K. Szendrei, V. Papay, I. Novak, and E. Minker, Tetrahedron Lett.,11, 3365 (1970).Google Scholar
  46. 46.
    J. Reisch, J. Korosi, K. Szendrei, I. Novak, and E. Minker, Phytochemistry,14, 2722 (1975).Google Scholar
  47. 47.
    J. G. Calvert and J. M. Pitts, Phytochemistry, Wiley, New York, 1966 [Russian translaton, Mir, Moscow (1968), p. 434].Google Scholar
  48. 48.
    J. J. McCullough, Chem. Rev.,87, 822 (1987).Google Scholar
  49. 49.
    A. Schönberg, Praparative Organische Photochemie, Springer-Verlag, Berlin (1958) [Russian translation, IL, Moscow (1963), p. 47].Google Scholar
  50. 50.
    A. V. Kamernitskii, V. N. Ignatov, and I. S. Levina, Usp. Khim.,57, No. 3, 474 (1988).Google Scholar
  51. 51.
    J. Reisch, A. Bathe, B. H. W. Rosenthal, and R. A. Salehi-Artimani, J. Heterocycl. Chem.,24, 869 (1987).Google Scholar

Copyright information

© Plenum Publishing Corporation 1989

Authors and Affiliations

  • I. A. Bessonova
  • S. Yu. Yunusov

There are no affiliations available

Personalised recommendations