Skip to main content
SpringerLink
Log in

Advances in the chemical synthesis of brassinosteroids

  • Published:
Chemistry of Natural Compounds Aims and scope

Abstract

This review generalizes the latest advances in the chemical synthesis of the plant growth regulators brassinosteroids in 1990–1994.

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

References

  1. N. V. Kovganko, Khim. Prir. Soedin., 159 (1991).

  2. N. V. Kovganko, Zh. Vses. Khim. Ob-va D. I. Mendeleeva,35, 440 (1991).

    Google Scholar 

  3. G. Adam and V. Marquardt, Z. Chem.,27, No. 2, 41 (1987).

    Google Scholar 

  4. S. Takatsuto and F. Futatsuya, J. Jpn. Oil Chem. Soc.,39, 227 (1990).

    Google Scholar 

  5. N. V. Kovganko and Zh. N. Kashkan, Khim. Prir. Soedin., 579 (1994).

  6. F. A. Lakhvich, V. A. Kripach, and V. N. Zhabinskii, Usp. Khim.,60, 1283 (1991).

    Google Scholar 

  7. A. V. Baranovskii, R. P. Litvinovskaya, and V. A. Kripach, Usp. Khim.,62, 704 (1993).

    Google Scholar 

  8. S. Takatsuto, Shokubutsu no Kagaku Chosetsu,29, 23 (1994); Chem. Abstr.,122, 10348 (1995).

    Google Scholar 

  9. H. G. Cutler, T. Uokota, and G. Adam, Brassinosteroids: Chemistry, Bioactivity and Applications, ACS Symposium Series 474, American Chemical Society, Washington, DC (1991).

    Google Scholar 

  10. V. A. Khripach, F. A. Lakhvich, and V. N. Zhabinskii, Brassinosteroids [in Russian], Navuka i Tékhnika, Minsk (1993).

    Google Scholar 

  11. T. Honda, K. Keino, and M. Tsubuki, J. Chem. Soc., Chem. Commun., 650 (1990).

  12. M. Tsubuki, K. Keino, and T. Honda, J. Chem. Soc., Perkin Trans. I, 2643 (1992).

    Google Scholar 

  13. T. G. Back and M. V. Krishna, J. Org. Chem.,56, 454 (1991).

    Google Scholar 

  14. T. G. Back, P. G. Blazecka, and M. V. Krishna, Can. J. Chem.,71, No. 2, 156 (1993).

    Google Scholar 

  15. M. Yuya and T. Takeuchi, Jpn. Pat. 64-75500 (1989).

  16. Z.-W. Shen and W.-S. Zhow, J. Chem. Soc., Perkin Trans. I, 1765 (1990).

    Google Scholar 

  17. W.-S. Zhow and L. Huang, Tetrahedron,48, 1837 (1992).

    Google Scholar 

  18. W.-S. Zhow and Z.-W. Shen, J. Chem. Soc., Perkin Trans. I, 2827 (1991).

    Google Scholar 

  19. Z. Shen and W. Zhow, Sci. China, Ser. B,35, 1181 (1992).

    Google Scholar 

  20. F. Jin, Y. Xu, and W. Huang, J. Chem. Soc., Perkin Trans. I, 795 (1993).

    Google Scholar 

  21. W.-S. Zhow, L.-F. Huang, L.-Q. Sun, and X.-F. Pan, Tetrahedron Lett.,32, 6745 (1991).

    Google Scholar 

  22. W.-S. Zhow, L.-F. Huang, L.-Q. Sun, and X.-F. Pan, J. Chem. Soc., Perkin Trans. I, 2039 (1992).

    Google Scholar 

  23. W.-S. Zhow, H.-Q. Zhow, G. Roussi, and Z.-Q. Wang, Synthesis, 1073 (1990)

  24. B. G. Hazra, V. S. Pore, and P. L. Joshi, J. Chem. Soc., Perkin Trans. I, 1819 (1993).

    Google Scholar 

  25. B. G. Hazra, N. P. Argade, and P. L. Joshi, Tetrahedron Lett.,33, 3375 (1992).

    Google Scholar 

  26. B. G. Hazra, P. L. Joshi, B. B. Bahdle, N. P. Argade, V. S. Pore, and M. D. Chordia, Tetrahedron,50, 2523 (1994).

    Google Scholar 

  27. T. Nakai and K. Mikami, Jpn. Pat. 02-180896 (1990); Chem. Abstr.,114, 43314 (1991).

    Google Scholar 

  28. T. G. Back, P. G. Blazecka, and M. V. Krishna, Tetrahedron Lett.,32, 4817 (1991).

    Google Scholar 

  29. V. A. Khripach, V. N. Zhabinskii, and E. V. Zhernosek, Tetrahedron Lett.,36, 607 (1995).

    Google Scholar 

  30. V. A. Khripach, R. P. Litvinovskaya, A. V. Baranovskii, and A. A. Akhrem, Russian Pat. 2,004,548 (1993).

  31. V. A. Khripach, R. P. Litvinovskaya, A. V. Baranovskii, and A. A. Akhrem, Russian Pat. 2,004,540 (1994).

  32. V. A. Khripach, R. P. Litvinovskaya, A. V. Baranovskii, and A. A. Akhrem, Dokl. Akad. Nauk SSSR,318, 597 (1981).

    Google Scholar 

  33. V. A. Khripach, V. N. Zhabinskii, and V. K. Olkhovick, Tetrahedron Lett.,31, 4937 (1990).

    Google Scholar 

  34. V. A. Khripach, V. N. Zhabinskii, and V. K. Ol'khovik, Zh. Org. Khim.,29, 2214 (1996).

    Google Scholar 

  35. T. Nakamura, K. Tanino, and I. Kuwayima, Tetrahedron Lett.,34, 477 (1993).

    Google Scholar 

  36. V. A. Khripach, M. I. Zavadskaya, A. I. Kotyatkina, and O. A. Drachenova, Zh. Org. Khim.,29, 1368 (1993).

    Google Scholar 

  37. V. A. Khripach, V. N. Zhabinskii, and A. I. Kotyatkina, Zh. Org. Khim.,30, 966 (1994).

    Google Scholar 

  38. W.-S. Zhow, L.-Q. Sun, and X.-F. Pan, Acta Chem. Sin.,50, 1192 (1992).

    Google Scholar 

  39. T. Kametani and T. Honda, Jpn. Pat. 64-29372 (1989).

  40. H. Abe and M. Yuya, Jpn. Pat 05-222090 (1991); Chem. Abstr.,120, 107478 (1994).

  41. H. Abe and M. Yuya, Jpn. Pat. 06-25281 (1992); Chem. Abstr.,120, 317801 (1994).

  42. S. Asakawa, H. Abe, Y. Kyokawa, S. Nakamura, and M. Natsume, Biosci., Bioechnol., Biochem.,58, 219 (1994).

    Google Scholar 

  43. T. Yokota, M. Nakayama, T. Wakisaka, J. Smidt, and G. Adam, Biosci., Biotechnol., Biochem.,58, 1183 (1994).

    Google Scholar 

  44. V. F. Traven', N. A. Kuznetsova, É. É. Levinson, and N. Ya. Podkhalyuzina, Dokl. Akd. Nauk SSSR,307, 901 (1991).

    Google Scholar 

  45. V. A. Khripach, N. V. Kovganko, T. A. Yanushkevich, A. I. Bykovets, S. L. Bykovets, and R. M. Zolotar', Russian Inventors' Certificate 1,360,114 (1993); Byul. Izobret., No. 43-44, 188 (1993).

  46. V. F. Traven', É. É. Levinson, and N. A. Kuznetsova, Dokl. Akad. Nauk SSSR,320, 1132 (1991).

    Google Scholar 

  47. V. A. Khripach, V. N. Zhabinskii, V. K. Ol'khovik, and E. V. Zhernosek, Russian Pat. 2,024,541 (1994).

  48. T. C. McMorris and P. A. Patil, J. Org. Chem.,58, 2338 (1993).

    Google Scholar 

  49. L. Kohout, Coll. Czech. Chem. Commun.,59, 457 (1994).

    Google Scholar 

  50. J. C. Ferrer, R. Lalueza, O. Saavedra, and C. Brosa, Tetrahedron Lett.,31, 3941 (1990).

    Google Scholar 

  51. V. A. Khripach, V. N. Zhabinskii, E. V. Zhernosek, F. A. Lakhvich, V. K. Ol'khovik, and G. V. Ivanova, Vestsi Akad. Navuk, Ser. Khim. Navuk, No. 2, 71 (1991).

    Google Scholar 

  52. A. Kolbe, V. Marquardt, and G. Adam, J. Labelled Comp. Radiopharm.,31, 860 (1992).

    Google Scholar 

  53. S. Seo, T. Nagasaki, Y. Katsuyama, F. Matsubara, T. Sakata, M. Yoshioka, and Y. Makisumi, J. Labelled Comp. Radiopharm.,27, 1383 (1989).

    Google Scholar 

  54. V. A. Khripach, V. N. Zhabinskii, and E. V. Zhernosek, Vestsi Akad. Navuk, Ser. Khim. Navuk, No. 6, 84 (1991).

    Google Scholar 

  55. V. A. Khripach, V. N. Zhabinskii, E. V. Zhernosek, and F. A. Lakhvich, USSR Inventors' Certificatate 1,594,181 (1990); Byull. Izobret., No. 35, 132 (1995).

  56. V. A. Khripach, V. N. Zhabinskii, and E. V. Zhernosek, Khim. Prir. Soedin., 90 (1992).

  57. H. Zhang, H. Zhang, and B. Pan, Chinese Pat. 1,039,594 (1988); Chem. Abstr.,114, 24323 (1991).

  58. E. E. Levinson, N. A. Kuznetsova, N. Y. Podhalyzina [Podkhalyuzina], and V. F. Traven, Mendeleev. Commun., No. 3, 96 (1994).

    Google Scholar 

  59. N. V. Kovganko and S. K. Ananich, Khim. Prir. Soedin., 224 (1992).

  60. N. V. Kovganov, O. P. Kananovich, and S. K. Ananich, Khim. Prir. Soedin., 667 (1992).

  61. S. Takatsuto, H. Sato, and F. Fatatsuya, US Pat. 4,961,775 (1990).

  62. S. Takatsuto, H. Sato, and F. Nitani, Jpn. Pat. 01-125396 (1989).

  63. F. A. Lakhvich, V. A. Khripach, N. V. Kovganko, and V. N. Zhabinskii, USSR Inventors' Cert. 1,270,154 (1986); Byull. Izobret., No. 42, 88 (1986)

  64. F. A. Lakhvich, V. A. Khripach, N. V. Kovganko, and V. N. Zhabinskii, USSR Inventors' Cert. 1,270,155 (1986); Byull. Izobret., No. 42, 88 (1986).

  65. F. A. Lakhvich, V. A. Khripach, N. V. Kovganko, and V. N. Zhabinskii, USSR Inventors' Cert. 1,363,830 (1993); Byull. Izobret., No. 43-44, 187 (1993).

  66. V. A. Khripach, V. N. Zhabinskii, G. V. Ivanova, and V. K. Ol'khovik, Vestsi Akad. Navuk, Ser. Khim. Navuk, No. 1, 70 (1992).

    Google Scholar 

  67. L. Song, J. Xie, and H. Zhang, Yingyong Huaxue,11, No. 3, 89 (1994); Chem. Abstr.,121, 231145 (1994).

    Google Scholar 

  68. C. Brosa, R. Peracaula, R. Puig, and M. Ventura, Tetrahedron Lett.,33, 7057 (1992).

    Google Scholar 

  69. L. Huang and W. Zhow, Chin. Chem. Lett.,3, 969 (1992).

    Google Scholar 

  70. L. Huang, W. Zhow, L. Sun, and X. Pan, J. Chem. Soc., Perkin Trans. I, 1683 (1993).

    Google Scholar 

  71. T. C. McMorris, P. A. Patil, R. G. Chavez, M. E. Baker, and S. D. Clouse, Phytochemistry,36, 585 (1994).

    Google Scholar 

  72. V. A. Khripach, V. N. Zhabinskii, and V. K. Ol'khovik, Khim. Prir. Soedin., 385 (1994).

  73. V. Fuendjiep, G. Charles, and D. Chriqui, Bull. Soc. Chim. Fr., 711 (1989).

  74. C. Brosa, S. Nusimovich, and R. Peracaula, Steroids,59, No. 8, 463 (1994).

    Google Scholar 

  75. A. A. Akhrem, F. A. Lakhvich, V. A. Khripach, N. V. Kovganko, V. N. Zhabinskii, A. I. Vykhovets, and M. P. Borisova, USSR Inventors' Cert. 1,433,005 (1991); Byull. Izobret., No. 48, 258 (1991).

  76. A. A. Akhrem, F. A. Lakhvich, V. A. Khripach, N. V. Kovganko, et al., USSR Inventors' Cert. 4,309,320 (1991); Byull. Izobret., No. 48, 256 (1991).

  77. Y. Kamuro, T. Kakiuchi, and S. Takatsuto, Jpn. Pat. 288,580 (1990).

    Google Scholar 

  78. N. V. Kovganko and S. K. Ananich, Khim. Prir. Soedin., 694 (1995).

  79. T. Furuta and Y. Yamamoto, J. Org. Chem.,57, 2981 (1992).

    Google Scholar 

  80. T. Nakai and K. Mikami, Jpn. Pat. 02-180895 (1989); Chem. Abstr.,114, 43313 (1991).

    Google Scholar 

  81. V. A. Khripach, R. P. Litvinovskaya, A. V. Baranovskii, and S. V. Drach, Zh. Org. Khim.,29, 724 (1993).

    Google Scholar 

  82. R. P. Litvinovskii, S. V. Drach, and V. A. Khripach, Zh. Org. Khim.,30, 304 (1994).

    Google Scholar 

  83. V. A. Khripach, R. P. Litvinovskaya, and S. V. Drach, Zh. Org. Khim.,29, 717 (1993).

    Google Scholar 

  84. V. Marquardt, G. Adam, M. F. Coll, and R. E. M. Alonso, GDR Pat., 273,638 (1989); Chem. Abstr.,112, 217353 (1990).

  85. W.-S. Tian, Acta Chim. Sin.,50, 72 (1992).

    Google Scholar 

  86. F. Coll, E. Alonso, M. Iglesias, V. Marquardt, and G. Adam, Rev. Cubana Quim.,6, 7 (1992).

    Google Scholar 

  87. L. T. Quyen, G. Adam, and K. Schreiber, Tetrahedron,50, 1923 (1994).

    Google Scholar 

  88. L. F. Huang and W. S. Zhow, J. Chem. Soc., Perkin Trans. I, 3579 (1994).

    Google Scholar 

  89. Y. Jiang, Z. Xu, and Q. Guo, Xiamen Daxul Xuebao, Ziran Kexueban,28, No. 3, 284 (1989); Chem. Abstr.,114, 24308 (1991).

    Google Scholar 

  90. B. Gao, Z. Wang, Q. Zheng, and Z. Xu, Acta Sci. Natur. Univ, Sutyatseni, Natur. Sci.,31, 55 (1992).

    Google Scholar 

  91. L. Kohout, Coll. Czech. Chem. Commun.,59, 1219 (1994).

    Google Scholar 

  92. L. Kohout and M. Stranad, Coll. Czech. Chem. Commun.,57, 1731 (1992).

    Google Scholar 

  93. L. Kohout and M. Strnad, Czechosl. Pat. 275,008 (1991).

    Google Scholar 

  94. S. Takatsuto and K. Shimazaki, Biosci., Biotechnol., Biochem.,56, 163 (1992).

    Google Scholar 

  95. R. Diziere, A. Tahri and D. Uguen, Tetrahedron Lett.,35, 3941 (1994).

    Google Scholar 

  96. L. Berthon, A. Tahri, and D. Uguen, Tetrahedron Lett.,35, 3937 (1994).

    Google Scholar 

  97. K. Mikami and S. Sakuda, J. Chem. Soc. Chem. Commun., 710 (1993).

Download references

Authors
  1. N. V. Kovganko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. K. Ananich
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Institute of Bioorganic Chemistry, Belarus Academy of Sciences, 220141, Minsk, ul. Zhodinskaya, 5/2. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 507–544, July–August, 1997.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kovganko, N.V., Ananich, S.K. Advances in the chemical synthesis of brassinosteroids. Chem Nat Compd 33, 389–416 (1997). https://doi.org/10.1007/BF02282358

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02282358

Keywords

Search

Navigation