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Russian Journal of General Chemistry

, Volume 83, Issue 10, pp 1874–1882 | Cite as

Catalytic hydrogenation of substituted 15β-Pregn-16-enes

  • A. V. Baranovskii
  • D. A. Bolibrukh
  • V. A. Khripach
Article

Abstract

The catalytic hydrogenation of 15-benzoyloxybutyl-20-hydroxymethylpregn-16-enes under various conditions was studied. It was shown that at the use of a palladium catalyst along with the reduction of the double bond also its shift occurred giving Δ14-derivatives. The reduction over a platinum catalyst is accompanied by the saturation of aromatic ring of the protecting group, but gives the best yield of the desired products and provides a preparative approach to 15-substituted analogs of brassinosteroids. The structures of the obtained compounds were proved by two-dimensional NMR spectroscopy and HPLC-MS.

Keywords

General Chemistry EtOAc Catalytic Hydrogenation Palladium Catalyst Epoxide Ring 
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.

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References

  1. 1.
    Litvinovskaya, R.P., Baranovskii, A.V., Aver’kova, M.A., and Khripach, V.A., Russ. J. Bioorg. Chem., 2007, vol. 33, no. 3, p. 320.CrossRefGoogle Scholar
  2. 2.
    Baranovskii, A.V. and Khripach, V.A., Russ. J. Gen. Chem., 2011, vol. 81, no. 10, p. 2142.CrossRefGoogle Scholar
  3. 3.
    Baranovsky, A.V., Bolibrukh, D.A., and Bull, J.R., Eur. J. Org. Chem., 2007, p. 445.Google Scholar
  4. 4.
    Baranovsky, A.V., Bolibrukh, D.A., Khripach, V.A., and Schneider, B., ARKIVOC, 2008, no. 9, p. 29.Google Scholar
  5. 5.
    Kobayashi, N., Higashi, T., and Shimada, K., J. Chem. Soc., Perkin Trans. 1, 1994, p. 269.Google Scholar
  6. 6.
    Konno, K., Ojima, K., Hayashi, T., and Takayama, H., Chem. Pharm. Bull., 1992, vol. 40, p. 1120.CrossRefGoogle Scholar
  7. 7.
    Castedo, L., Granja, J.R., and Mourino, A., Tetrahedron Lett., 1985, vol. 26, p. 4959.CrossRefGoogle Scholar
  8. 8.
    Castedo, L., Granja, J.R., Mourino, A., and Pumar, M.C., Synth. Comm., 1987, vol. 17, p. 251.CrossRefGoogle Scholar
  9. 9.
    Dauben, W.G. and Brookhart, T., J. Org. Chem., 1982, vol. 47, p. 3921.CrossRefGoogle Scholar
  10. 10.
    Mikami, K., Kishino, H., Matsueda, H., and Loh, T.P., Synlett, 1993, p. 497.Google Scholar
  11. 11.
    Kim, H.S., Wilson, W.K., Needleman, D.H., Pinkerton, F.D., Wilson, D.K., Quiocho, F.A., and Schroepfer, G.J., J. Lipid. Res., 1989, vol. 30, p. 247.Google Scholar
  12. 12.
    Izzo, I., Di Filippo, M., Napolitano, R., and De Riccardis, F., Eur. J. Org. Chem., 1999, p. 3505.Google Scholar
  13. 13.
    Dayal, B., Ertel, N.H., Rapole, K.R. Asgaonkar, A., and Salen, G., Steroids, 1997, vol. 62, p. 451.CrossRefGoogle Scholar
  14. 14.
    Rao, H.S.P. and Reddy, K.S., Tetrahedron Lett., 1994, vol. 35, p. 171.CrossRefGoogle Scholar
  15. 15.
    Gorzynski Smith, J., Synthesis, 1984, no. 8, p. 629.Google Scholar
  16. 16.
    Collins, D.J. and Sjovall, J., Tetrahedron Lett., 1979, no. 7, p. 639.Google Scholar
  17. 17.
    Organic Reactions in Steroid Chemistry, Fried, J. and Edwards, J.A., Eds., New York: van Nostrand Reinhold Company, 1972, vol. 2, p. 6.Google Scholar
  18. 18.
    Kamano, Y., Nogawa, T., Yamashita, A., Hayashi, M., Inoue, M., Drasar, P., and Pettit, G.R., J. Nat. Prod., 2002, vol. 65, p. 1001.CrossRefGoogle Scholar
  19. 19.
    Kamano, Y., Nogawa, T., Yamashita, A., and Pettit, G.R., Collect. Czech. Chem. Commun., 2001, vol. 66, p. 1841.CrossRefGoogle Scholar
  20. 20.
    Atta-ur-Rahman, Jamal, S.A., and Choudhary, M.I., Heterocycles, 1992, vol. 34, p. 689.CrossRefGoogle Scholar
  21. 21.
    Ogawa, S., Hosoi, K., Iida, T., Wakatsuki, Y., Makino, M., Fujimoto, Y., and Hofmann, A.F., Eur. J. Org. Chem., 2007, no. 21, p. 3555.Google Scholar
  22. 22.
    Hazra, B.G., Pore, V.S., and Joshi, P.L., J. Chem. Soc., Perkin. Trans. 1, 1993, no. 15, p. 1819.Google Scholar
  23. 23.
    Hazra, B.G., Joshi, P.L., Bahule, B.B., Argade, N.P., Pore, V.S., and Chordia, M.D., Tetrahedron, 1994, vol. 50, no. 8, p. 2523.CrossRefGoogle Scholar
  24. 24.
    Armarego, W.L.F. and Chai, C.L.L., Purification of Laboratory Chemicals, Oxford: Pergamon Press, 2003.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2013

Authors and Affiliations

  • A. V. Baranovskii
    • 1
  • D. A. Bolibrukh
    • 1
  • V. A. Khripach
    • 1
  1. 1.Institute of Bioorganic ChemistryNational Academy of Sciences of BelarusMinskBelarus

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