Skip to main content
SpringerLink
Log in

Skeletal rearrangements in steroids and polycyclic triterpenoids (review)

  • Published:
Pharmaceutical Chemistry Journal Aims and scope

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

Literature cited

  1. A. V. Kamernitskii, I. G. Reshetova, S. V. Chernov, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 11, 2596 (1984).

    Google Scholar 

  2. D. Y. Aberhart, Tay-Yuan Chau, and E. Caspi, J. Chem. Soc. Perkin Trans. 1, 220 (1979).

    Google Scholar 

  3. R. U. Almaula, G. K. Triverdi, and S. C. Bhattacharyya, Indian J. Chem. B,16, 257 (1978).

    Google Scholar 

  4. A. Ambles and R. Jacquesy, Bull. Soc. Chim. France,804. (1972).

  5. M. Anastasia, A. Fiecchi and A. Scala, J. Org. Chem.,43, 3505 (1978).

    Google Scholar 

  6. M. Anastasia, A. M. Soave, and A. Scala, J. Chem. Soc, 1131 (1979).

  7. G. V. Baddeley, H. Y. Saman, Y. Y. Simes, and Tu Hoa Ai, J. Chem. Soc., 7 (1979).

  8. P. A. Barlett and W. S. Johnson, J. Am. Chem. Soc.,95, 7501 (1973).

    Google Scholar 

  9. E. T. Bathurst, J. M. Coxon, et al., Aust. J. Chem.,27, 1505 (1974).

    Google Scholar 

  10. E. T. Bathurst and J. M. Coxon, Chem. Commun., 131 (1974).

  11. G. Berti, S. Catalano, et al., Tetrahedron Lett., 401 (1976).

  12. S. Bertozzi, S. Catalano, et al., Ann. Chim. (Roma), 439 (1973).

  13. S. C. Bhattacharyya and I. Kitagawa, Indian J. Chem. B.,11, 1249 (1973).

    Google Scholar 

  14. E. T. Brunke, R. Böhm, et al., Chem. Ber.,111, 1404 (1974).

    Google Scholar 

  15. A. Campbell and C. Hewett, J. Chem. Soc Perkin Trans. 1, 1799 (1974).

    Google Scholar 

  16. E. Caspi, W. L. Duax, and Y. F. Griffin, Chem. Pharm. Bull.,26, 2281 (1978).

    Google Scholar 

  17. A. Chatterjee, S. Mukhopadhyay, et al., Tetrahedron,32, 3051 (1976).

    Google Scholar 

  18. A. Chatterjeee, S. K. Saha, Indian J. Chem. B,16, 1038 (1978).

    Google Scholar 

  19. C. Chavis, J. Marchand, et al., Tetrahedron,33, 2651 (1977).

    Google Scholar 

  20. R. W. Coombs, W. Koletar, et al., J. Chem. Soc. Perkin Trans. 1, 792 (1975).

    Google Scholar 

  21. Y. M. Coxon, M. P. Hartshorn, and C. N. Muir, Chem. Commun., 1591 (1970).

  22. Y. M. Coxon and Y. R. Gibson, Aust. J. Chem.,32, 2223 (1979).

    Google Scholar 

  23. Y. M. Coxon and Y. R. Gibson, Aust. J. Chem.,33, 2577 (1981).

    Google Scholar 

  24. B. W. Cubberley, I. G. Quest, J. G. Jones, et al., J. Chem. Soc Perkin Trans. 1, 1916 (1977).

    Google Scholar 

  25. W. G. Dauben, G. Ahlgren, and T. Leitereg, J. Am. Chem. Soc,94, 8593 (1972).

    Google Scholar 

  26. W. A. Denny, V. Kumar and Q. Meakins, J. Chem. Soc. Perkin Trans. I, 486 (1972).

    Google Scholar 

  27. O. E. Edwards, Stud. Org. Chem.,20, 51 (1985).

    Google Scholar 

  28. D. E. Ekong and M. D. Selema, J. Chem. Soc. Perkin Trans. I, 1084 (1972).

    Google Scholar 

  29. B. Epe and A. Mondon, Tetrahedron Lett., 2015 (1979).

  30. R. W. Foster and B. A. Marples, Tetrahedron Lett., 2071 (1979).

  31. F. Frappier, J. Boivin, and F. Jareau, C. R. Acad. Sci.,274C, 2190 (1982).

    Google Scholar 

  32. F. Frappier, M. Audinot, and J. P. Beacourt, J. Org. Chem.,47, 3783 (1982).

    Google Scholar 

  33. G. Habermehl and W. Walz, Z. Naturforsch.,31, 983 (1976).

    Google Scholar 

  34. T. G. Halsall and R. J. Eston, Chem. Commun., 3223 (1972).

  35. W. S. Hancock and L. N. Menger, Tetrahedron Lett., 3223 (1971).

  36. R. Hanna, Tetrahedron Lett., 3349 (1971).

  37. K. Iguchi and H. Kakisava, Chem. Commun., 1488 (1970).

  38. J. G. Jones and B. A. Marples, J. Chem. Soc. Perkin Trans. I, 792 (1972).

    Google Scholar 

  39. D. N. Kirk and M. P. Hartshorn, Steroid Reaction Mechanisms Amsterdam (1968), p. 261.

  40. D. N. Kirk and P. M. Shaw, J. Chem. Soc. Perkin Trans. I, 2284 (1975).

    Google Scholar 

  41. P. Kocovsky and V. Cerny, Coll. Czhech. Chem. Commun.,41, 2620 (1976).

    Google Scholar 

  42. P. Kocovsky and V. Cerny, Coll. Czhech. Chem. Commun.,42, 2425 (1977).

    Google Scholar 

  43. P. Kocovsky, Chem. Listy,73, 583 (19790).

  44. P. Kocovsky, V. Cerny, and F. Turecek, Coll. Czech. Chem. Commun.,44, 234 (1979).

    Google Scholar 

  45. F. Kohen, R. A. Mallory, and Y. Scheer, J. Org. Chem.,36, 716 (1971).

    Google Scholar 

  46. L. P. Makhubu, Z. G. Hajos, and G. R. Duncan, Chem. Pharm. Bull.,20, 2511 (1972).

    Google Scholar 

  47. B. A. Marples, B. M. O'Callaghan, and Y. L. Scottow, J. Chem. Soc. Perkin Trans. I, 1026 (1974).

    Google Scholar 

  48. R. G. McQeen and T. R. Watson, Chem. Pharm. Bull.,28, 1999 (1980).

    Google Scholar 

  49. Molecular Rearrangements, Vol. 1–2, P. de Mayo, editor, New York (1967), p. 813.

  50. C. Monneret, Q. Khuong-Huu, et al., Bull. Soc. Chim. Fr., 291 (1972).

  51. S. Morelli and S. Catalano, Gazz. Chim. Ital.,102, 636 (1972).

    Google Scholar 

  52. S. Morelli and S. Catalano, Gazz. Chim. Ital.,102, 793 (1972).

    Google Scholar 

  53. S. Morelli and S. Catalano, Gazz. Chim. Ital.,102, 572 (1972).

    Google Scholar 

  54. S. Morelli, S. Catalano, et al., Tetrahedron Lett., 717 (1972).

  55. D. Mukherjee and C. R. Engel, Can, J. Chem.,52, 1744 (1974).

    Google Scholar 

  56. Y. Nakatani, G. Pousinet, G. Wolff, et al., Tetrahedron,28, 4249 (1972).

    Google Scholar 

  57. E. Noyer, J. Bascoul, and C. Paulet, J. Steroid Biochem.,7, 631 (1976).

    Google Scholar 

  58. R. Ofuchi, N. Kawahara, and I. Yoshikawa, Chem. Pharm. Bull.,26, 2262 (1978).

    Google Scholar 

  59. Su. Ohta, Y. Moriyama, and T. Tsuyuki, Chem. Pharm. Bull., No. 10, 1617 (1982).

    Google Scholar 

  60. Su. Ohta, Y. Moriyama, and T. Tsuyuki, Chem. Abstr.,100, No. 192108 (1984).

  61. G. Ortar and A. Romeo, J. Org. Chem.,41, 4036 (1976).

    Google Scholar 

  62. Z. Paryzek, Can. J. Chem.,53, 3498 (1975).

    Google Scholar 

  63. Z. Paryzek, Tetrahedron Lett., 4761 (1976).

  64. Z. Paryzek, Bull. Acad. Pol. Sci., Ser. Chim.,26, 583 (1978).

    Google Scholar 

  65. Z. Paryzek, Bull. Acad. Pol. Sci., Ser. Chim.,26, 591 (1978).

    Google Scholar 

  66. Z. Paryzek, J. Chem. Soc. Perkin Trans. I, 1222 (1979).

    Google Scholar 

  67. Z. Paryzek and R. Wydra, Steroids,38, 141 (1981).

    Google Scholar 

  68. Z. Paryzek and O. E. Edwards, Can. J. Chem.,61, 1973 (1983).

    Google Scholar 

  69. Z. Paryzek, R. Wydra, and K. Blaszcyk, Chem. Lett., 1171 (1983).

  70. Z. Paryzek and R. Wydra, Can. J. Chem.,63, 1280 (1985).

    Google Scholar 

  71. T. M. Peakman, N. A. Lamb, and Y. R. Maxwell, Tetrahedron, Lett., 349 (1984).

  72. G. R. Pettit, T. R. Kasturi, and Y. C. Knight, J. Org. Chem.,35, 1404 (1970).

    Google Scholar 

  73. T. Prange, C. Pscard, G. Sozzi, et al., Tetrahedron Lett., 245 (1977).

  74. I. G. Quest and B. A. Marples, J. Chem. Soc. C, 1468 (1977).

  75. J. Schmitt, A. Hallot, P. Cornu, et al., Bull. Soc. Chim. Fr., 2032 (1973).

  76. J. Schmitt, A. Hallot, P. Cornu, et al., Bull. Soc. Chim. Fr., 2035 (1973).

  77. A. Schwartz and E. J. Glotter, J. Chem. Soc. Perkin Trans. I, 2470 (1977).

    Google Scholar 

  78. P. Sengupta, M. M. Sen, and M. U. Sakar, J. Chem. Soc. Perkin Trans. I, 384 (1978).

    Google Scholar 

  79. R. C. Sheppard and S. Turner, J. Chem. Soc. Perkin Trans. I, 2551 (1977).

    Google Scholar 

  80. O. Sieskind and P. Albrecht, Tetrahedron Lett., No. 26, 2135 (1985).

    Google Scholar 

  81. E. Suckas and T. Hase, Acta Chem. Scand.,31, 231 (1977).

    Google Scholar 

  82. A. Takadate and J. Fishman, Tetrahedron,27, 2217 (1971).

    Google Scholar 

  83. T. Takahasi and K. Tashibana, Tetrahedron Lett., 1857 (1971).

  84. D. M. Tal, E. Keinan, and Y. Maeur, Tetrahedron,37, 4327 (1981).

    Google Scholar 

  85. M. Tori, Y. Moriyama, and T. Tsuyuki, Bull. Chem. Soc. Jpn.,50, 1552 (1977).

    Google Scholar 

  86. M. Tori, T. Tsuyuki, and T. Takahashi, Bull. Chem. Soc. Jpn.,50, 3381 (1977).

    Google Scholar 

  87. I. Wicha, Tetrahedron Lett., 2877 (1977).

  88. Y. Yagodzinsky, Y. Gumulka, W. Szchepek, et al., Tetrahedron,37, 1015 (1981).

    Google Scholar 

  89. Y. Yokoyama, Y. Moriyama, T. Tsuyuki, et al., Chem. Lett.,67, (1980).

  90. J. L. Zundel, G. Wolff, and G. Ourisson, Bull. Soc. Chim. Fr., 3206 (1973).

Download references

Author information

Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    A. V. Kamernitskii, I. G. Reshetova & S. V. Chernov

Authors
  1. A. V. Kamernitskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I. G. Reshetova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. S. V. Chernov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiko-farmatsevticheskii Zhurnal., Vol. 21, No. 10, pp. 1239–1248, October, 1987.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kamernitskii, A.V., Reshetova, I.G. & Chernov, S.V. Skeletal rearrangements in steroids and polycyclic triterpenoids (review). Pharm Chem J 21, 736–744 (1987). https://doi.org/10.1007/BF00758138

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00758138

Keywords

Search

Navigation