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Methods of the synthesis of A-seco derivatives of pentacyclic triterpenoids

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Abstract

The review considers the main methods for the synthesis of derivatives of A-seco pentacyclic triterpenoids by means of the Baeyer-Villiger reaction, the Beckmann rearrangement, and other oxidation processes.

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References

  1. P. Dzubak, M. Hajduch, D. Vydra, A. Hustova, M. Kvasnica, D. Biedermann, L. Markova, M. Urban, J. Sarek, Nat. Prod. Rep., 2006, 23, 394.

    Article  CAS  Google Scholar 

  2. L. A. Baltina, R. M. Kondratenko, L. A. Baltina (ml.), O. A. Plyasunova, A. G. Pokrovskii, G. A. Tolstikov, Khim.-farm. Zh., 2009, 10, 3 [Pharm. Chem. J. (Engl. Transl.), 2009, 10, 539].

    Google Scholar 

  3. F. Soler, C. Poujade, M. Evers, J. C. Carry, Y. Hénin, A. Bousseau, T. Huet, R. Pauwels, E. De Clercq, J. F. Mayaux, J. B. Le Pecq, N. Dereu, J. Med. Chem., 1996, 39, 1069.

    Article  CAS  Google Scholar 

  4. Y. Kashiwada, F. Hashimoto, L. M. Cosentino, C. H. Chen, P. E. Garrett, K. H. Lee, J. Med. Chem., 1996, 39, 1016.

    Article  CAS  Google Scholar 

  5. P. A. Krasutsky, Nat. Prod. Rep., 2006, 23, 919.

    Article  CAS  Google Scholar 

  6. R. F. Taylor, Microbiol. Rev., 1984, 48, 181.

    CAS  Google Scholar 

  7. G. A. Tolstikov, L. A. Baltina, N. G. Serdyuk, Khim.-farm. Zh., 1998, 8, 5 [Pharm. Chem. J. (Engl. Transl.), 1998, 8, 402].

    Google Scholar 

  8. T. G. Tolstikova, I. V. Sorokina, G. A. Tolstikov, A. G. Tolstikov, O. B. Flekhter, Bioorg. Khim. 2006, 1, 42 [Russ. J. Bioorg. Chem. (Engl. Transl.), 2006, 1, 37].

    Google Scholar 

  9. T. G. Tolstikova, I. V. Sorokina, G. A. Tolstikov, A. G. Tolstikov, O. B. Flekhter, Bioorg. Khim. 2006, 3, 291 [Russ. J. Bioorg. Chem. (Engl. Transl.), 2006, 3, 261].

    Google Scholar 

  10. G. A. Tolstikov, O. B. Flekhter, E. E. Shul’ts, L. A. Baltina, A. G. Tolstikov, Khim. Interes. Ustoichivogo Razvitiya, 2005, 1, 1 [Chem. Sustain. Dev. (Engl. Transl.), 2005, 1, 1].

    Google Scholar 

  11. W. Baas, Phytochemistry, 1985, 24, 1875.

    Article  CAS  Google Scholar 

  12. Preferred IUPAC Names, 2004, № 10; http://old.iupac.org/reports/provisional/abstract04/BB-prs310305/Chapter10.pdf (query date 18.05.2010).

  13. J. Simonsen, W. C. Ross, The Terpenes, Vol. IV, Cambridge University Press, Cambridge, 1956, 524.

    Google Scholar 

  14. D. Arigoni, D. H. Barton, R. Bernasconi, C. Djerassi, J. S. Mills, R. E. Wolff, J. Chem. Soc. (R), 1960, 1900.

    Google Scholar 

  15. G. H. Whitham, J. Chem. Soc. (R), 1960, 2016.

    Google Scholar 

  16. A. I. Laskin, P. Grabowich, C. D. Meyers, J. Fried, J. Med. Chem., 1964, 7, 406.

    Article  CAS  Google Scholar 

  17. T. A. Hase, R. Huikko, Acta Chem. Scand., Ser. B, 1978, 32, 467.

    Article  Google Scholar 

  18. R. Uusvuori, T. Hase, Synth. Commun., 1982, 12, 1081.

    Article  CAS  Google Scholar 

  19. T. Takahashi, G. Ourisson, Bull. Soc. Chim. Fr., 1956, 353.

    Google Scholar 

  20. J. Sejbal, J. Klinot, D. Hrncirova, A. Vystrcil, Collect. Czech. Chem. Commun., 1985, 50, 2753.

    Article  CAS  Google Scholar 

  21. M. Kvasnica, I. Tišlerová, J. Šarek, J. Sejbal, I. Císařová, Collect. Czech. Chem. Commun., 2005, 70, 1447.

    Article  CAS  Google Scholar 

  22. T. Nishihama, T. Takahashi, Bull. Chem. Soc. Jpn, 1987, 60, 2117.

    Article  CAS  Google Scholar 

  23. Y. Ku, G. Rao, C. Chen, C. Wu, J. Guh, S. Lee, Helv. Chim. Acta, 2003, 86, 697.

    Article  CAS  Google Scholar 

  24. F. Lugemwa, F. Huang, M. Bentley, M. Mendel, A. Alford, J. Agric. Food Chem., 1990, 38, 493.

    Article  CAS  Google Scholar 

  25. C. Moiteiro, M. J. Curto, N. Mohamed, M. Bailén, R. Martínez-Díaz, A. González-Coloma, J. Agric. Food Chem., 2006, 54, 3566.

    Article  CAS  Google Scholar 

  26. R. Stevenson, J. Org. Chem., 1963, 28, 188.

    Article  CAS  Google Scholar 

  27. N. I. Medvedeva, O. B. Flekhter, E. V. Tret’yakova, F. Z. Galinin, L. A. Baltina, L. V. Spirikhin, G. A. Tolstikov, Zh. Org. Khim., 2004, 8, 1140 [Russ. J. Org. Chem. (Engl. Transl.), 2004, 8, 1092].

    Google Scholar 

  28. A. Patra, S. Chaudhuri, Magn. Reson. Chem., 1987, 25, 95.

    Article  CAS  Google Scholar 

  29. J. Fried, G. W. Krakower, R. David, H. Basch, J. Med. Chem., 1965, 8, 279.

    Article  CAS  Google Scholar 

  30. D. Maitraie, C. Hung, H. Tu, Y. Liou, B. Wei, S. Yang, J. Wang, C. Lin, Bioorg. Med. Chem., 2009, 17, 2785.

    Article  CAS  Google Scholar 

  31. B. P. Pradhan, S. Chakraborty, Tetrahedron Lett., 1989, 30, 5463.

    Article  CAS  Google Scholar 

  32. A. Patra, S. K. Chaudhuri, Ind. J. Chem., Sect. B, 1989, 28, 376.

    Google Scholar 

  33. M. Tori, R. Matsuda, M. Sono, Y. Kohama, Y. Asakawa, Bull. Chem. Soc. Jpn, 1988, 61, 2103.

    Article  CAS  Google Scholar 

  34. T. Hase, J. Chem. Soc., Chem. Commun., 1972, 755.

    Google Scholar 

  35. S. Dutta, S. C. Ray, Ind. J. Chem., Sect. B, 1991, 30, 513.

    Google Scholar 

  36. I. Valterova, J. Klinot, A. Vystrcil, Collect. Czech. Chem. Commun., 1980, 45, 1964.

    Article  CAS  Google Scholar 

  37. X. Wen, P. Zhang, J. Liu, L. Zhang, X. Wu, P. Ni, H. Sun, Bioorg. Med. Chem. Lett., 2006, 16, 722.

    Article  CAS  Google Scholar 

  38. J. Klinot, J. Sejbal, A. Vystrcil, Collect. Czech. Chem. Commun., 1989, 54, 400.

    Article  CAS  Google Scholar 

  39. J. Sejbal, E. Klinotová, M. Bludska, J. Klinot, M. Budesinsky, Collect. Czech. Chem. Commun., 1989, 54, 1036.

    Article  CAS  Google Scholar 

  40. M. Kvasnica, I. Rudovska, M. Hajduch, J. Sarek, Monatsh. Chem. (Chem. Month.), 2010, 141, 233.

    Article  CAS  Google Scholar 

  41. A. D. McNaught, A. Wilkinson, in IUPAC. Compendium of Chemical Terminology (the “Gold Book”), Blackwell Scientific Publications, Oxford, 1997, 2, 1332.

    Google Scholar 

  42. C. W. Cumper, G. B. Leton, A. I. Vogel, J. Chem. Soc. (R), 1965, 2067.

    Google Scholar 

  43. A. V. Korovin, A. V. Tkachev, Russ. Chem. Bull. (Int. Ed.), 2001, 50, 304 [Izv. Akad. Nauk. Ser. Khim., 2001, 292].

    Article  CAS  Google Scholar 

  44. J. Hao, X. Zhang, P. Zhang, J. Liu, L. Zhang, H. Sun, Tetrahedron, 2009, 65, 7975.

    Article  CAS  Google Scholar 

  45. J. Hao, P. Zhang, X. Wen, H. Sun, J. Org. Chem., 2008, 73, 7405.

    Article  CAS  Google Scholar 

  46. Y. Wei, C. Ma, M. Hattori, Eur. J. Med. Chem., 2009, 44, 4112.

    Article  CAS  Google Scholar 

  47. A. K. Ganguly, T. R. Govindachari, P. A. Mohamed, Tetrahedron, 1966, 22, 3579.

    Google Scholar 

  48. S. K. Kundu, A. Chatterjee, A. S. Rao, Chem. Ber., 1968, 101, 3255.

    Article  CAS  Google Scholar 

  49. M. Urban, J. Sarek, J. Klinot, G. Korinkova, M. Hajduch, J. Nat. Prod., 2004, 67, 1100.

    Article  CAS  Google Scholar 

  50. M. Evers, C. Poujade, F. Soler, Y. Ribeill, C. James, Y. Lelièvre, J. C. Gueguen, D. Reisdorf, I. Morize, R. Pauwels, E. De Clercq, Y. Hénin, A. Bousseau, J. F. Mayaux, J. B. Le Pecq, N. Dereu, J. Med. Chem., 1996, 39, 1056.

    Article  CAS  Google Scholar 

  51. T. Nishihama, T. Takahashi, Bull. Chem. Soc. Jpn, 1966, 39, 200.

    Article  CAS  Google Scholar 

  52. T. Kikuchi, M. Niwa, Tetrahedron Lett., 1971, 12, 3807.

    Article  Google Scholar 

  53. T. Kikuchi, T. Toyoda, Chem. Pharm. Bull., 1971, 19, 753.

    Article  CAS  Google Scholar 

  54. T. Kikuchi, T. Toyoda, Tetrahedron Lett., 1967, 3183.

    Google Scholar 

  55. Y. Deng, J. K. Snyder, J. Org. Chem., 2002, 67, 2864.

    Article  CAS  Google Scholar 

  56. T. Honda, G. W. Gribble, N. Suh, H. J. Finlay, B. V. Rounds, L. Bore, F. G. Favaloro, Y. Wang, M. B. Sporn, J. Med. Chem., 2000, 43, 1866.

    Article  CAS  Google Scholar 

  57. M. Urban, J. Sarek, I. Tislerova, P. Dzubak, M. Hajduch, Bioorg. Med. Chem., 2005, 13, 5527.

    Article  CAS  Google Scholar 

  58. M. Endová, E. Klinotová, J. Sejbal, B. Máca, J. Klinot, J. Protiva, Collect. Czech. Chem. Commun., 1994, 59, 1420.

    Article  Google Scholar 

  59. J. Lehn, G. Ourisson, Bull. Soc. Chim. Fr., 1962, 1133.

    Google Scholar 

  60. Y. Wei, C. Ma, M. Hattori, Bioorg. Med. Chem., 2009, 17, 3003.

    Article  CAS  Google Scholar 

  61. C. Moiteiro, C. Manta, F. Justino, R. Tavares, M. J. Curto, M. Pedro, M. S. Nascimento, M. Pinto, J. Nat. Prod., 2004, 67, 1193.

    Article  CAS  Google Scholar 

  62. B. P. Mundy, M. G. Ellerd, F. G. Favaloro, in Name Reactions and Reagents in Organic Synthesis, J. Wiley and Sons, Hoboken, 2005, 2, 80.

    Book  Google Scholar 

  63. G. P. Moss, S. A. Nicolaidis, J. Chem. Soc. D, 1969, 1077.

    Google Scholar 

  64. T. Hase, Acta Chem. Scand., 1970, 24, 364.

    Article  CAS  Google Scholar 

  65. G. A. Tolstikov, Kh. A. Alibaeva, M. I. Goryaev, Zh. Org. Khim., 1969, 5, 1625 [J. Org. Chem. USSR (Engl. Transl.), 1969, 5].

    CAS  Google Scholar 

  66. O. B. Flekhter, N. I. Medvedeva, G. A. Tolstikov, O. V. Savinova, E. I. Boreko, F. M. Dolgushin, Zh. Bioorg. Khim., 2009, 35, 122 [Russ. J. Bioorg. Chem. (Engl. Transl.), 2009, 35, 118].

    Google Scholar 

  67. T. Honda, G. W. Gribble, J. Org. Chem., 1998, 63, 4846.

    Article  CAS  Google Scholar 

  68. K. F. Cohen, R. Kazlauskas, J. T. Pinhey, J. Chem. Soc., Perkin Trans. 1, 1973, 2076.

    Google Scholar 

  69. M. Draínsky, S. Hybelbauerová, J. Sejbal, M. Buděšínský, Collect. Czech. Chem. Commun., 2006, 71, 1131.

    Article  Google Scholar 

  70. E. Klinotová, V. Křeček, J. Klinot, M. Endová, J. Eisenreichová, M. Buděššínský, M. Štícha, Collect. Czech. Chem. Commun., 1997, 62, 1776.

    Article  Google Scholar 

  71. R. Kasai, K. Matsumoto, S. Taniyasu, O. Tanaka, J. Kim, D. Hahn, Chem. Pharm. Bull., 1986, 34, 3284.

    Article  CAS  Google Scholar 

  72. A. Wahhab, M. Ottosen, F. Bachelor, Can. J. Chem., 1991, 69, 570.

    Article  CAS  Google Scholar 

  73. R. Carman, D. E. Cowley, Tetrahedron Lett., 1964, 5, 627.

    Article  Google Scholar 

  74. G. A. Tolstikov, M. I. Goryaev, Zh. Org. Khim., 1966, 2, 1718 [J. Org. Chem. USSR (Engl. Transl.), 1966, 2].

    CAS  Google Scholar 

  75. G. A. Tolstikov, Kh. A. Alibaeva, V. M. Potapov, Zh. Org. Khim., 1969, 5, 1631 [J. Org. Chem. USSR (Engl. Transl.), 1969, 5].

    CAS  Google Scholar 

  76. V. R. Akhmetova, E. R. Shakurova, L. M. Khalilov, Zh. Org. Khim., 2009, 4, 634 [Russ. J. Org. Chem. (Engl. Transl.), 2009, 4, 621].

    Google Scholar 

  77. S. Huneck, Chem. Ber., 1965, 98, 1837.

    Article  CAS  Google Scholar 

  78. I. A. Tolmacheva, V. V. Grishko, E. I. Boreko, O. V. Savinova, N. I. Pavlova, Khim. Prirod. Soedin., 2009, 5, 566 [Chem. Nat. Compd. (Engl. Transl.), 2009, 5, 673].

    Google Scholar 

  79. I. A. Tolmacheva, A. V. Nazarov, O. A. Maiorova, V. V. Grishko, Khim. Prirod. Soedin., 2008, 5, 491 [Chem. Nat. Compd. (Engl. Transl.), 2008, 5, 606].

    Google Scholar 

  80. L. Zaprutko, Pol. J. Chem., 1994, 68, 1753.

    CAS  Google Scholar 

  81. J. Sejbal, M. Homolová, I. Tišlerová, V. Křeček, Collect. Czech. Chem. Commun., 2000, 65, 1339.

    Article  CAS  Google Scholar 

  82. L. Zaprutko, Pol. J. Chem., 1995, 69, 1003.

    CAS  Google Scholar 

  83. C. Moiteiro, F. Justino, R. Tavares, M. J. Marcelo-Curto, M. H. Florêncio, M. S. Nascimento, M. Pedro, F. Cerqueira, M. M. Pinto, J. Nat. Prod., 2001, 64, 1273.

    Article  CAS  Google Scholar 

  84. J. C. Turner, Chem. Commun. (London), 1967, 396.

    Google Scholar 

  85. A. V. Shernyukov, I. Ya. Mainagashev, D. V. Korchagina, Yu. V. Gatilov, N. F. Salakhutdinov, G. A. Tolstikov, Khim. Prirod. Soedin., 2012, 5, 732 [Chem. Nat. Compd. (Engl. Transl.), 2012, 5, 821].

    Google Scholar 

  86. O. Dischendorfer, O. Polak, Monatsh. Chem., 1929, 51, 43.

    Article  CAS  Google Scholar 

  87. O. Dischendorfer, H. Juvan, Monatsh. Chem., 1930, 56, 272.

    Article  CAS  Google Scholar 

  88. L. Ruzicka, G. F. Frame, H. M. Leicester, M. Liguori, H. Brungger, Helv. Chim. Acta, 1934, 17, 426.

    Article  CAS  Google Scholar 

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Correspondence to A. V. Shernyukov.

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Dedicated to Academician of the Russian Academy of Sciences I. P. Beletskaya on the occasion of her anniversary.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 0880–0896, April, 2013.

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Shernyukov, A.V., Salakhutdinov, N.F. & Tolstikov, G.A. Methods of the synthesis of A-seco derivatives of pentacyclic triterpenoids. Russ Chem Bull 62, 878–895 (2013). https://doi.org/10.1007/s11172-013-0120-3

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