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Synthesis of 6-deoxo-24-epiteasterone and its analogs

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Abstract

Selective reduction of the C8=C14 double bond in 3-hydroxyergosta-8(14),22-dien-15-one, followed by cis-hydroxylation of the double bond in the side chain and reduction of the 15-oxo group gave new 3β-hydroxy-6-deoxobrassinosteroids, their 22S,23S isomers, and the corresponding esters. The side chain in the products is identical to that in such known natural brassinosteroids as 24-epibrassinolide and 24-epicastasterone.

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References

  1. Yokota, T., Morita, M., and Takahashi, N., Agric. Biol. Chem., 1983, vol. 47, p. 2149.

    CAS  Google Scholar 

  2. Yokota, T., Koba, S., Kim, S.K., and Takatsuto, S., Agric. Biol. Chem., 1987, vol. 51, p. 1625.

    CAS  Google Scholar 

  3. Kim, S.K., Brassinosteroids: Chemistry, Bioactivity, and Applications, Cutler, H.G., Yokota, T., and Adam, G., Eds., Washington, DC: Am. Chem. Soc., 1991, ACS Symp. Series, vol. 474, p. 26.

    Google Scholar 

  4. Spengler, B., Schmidt, J., Voigt, B., and Adam, G., Phytochemistry, 1995, vol. 40, p. 907.

    Article  CAS  Google Scholar 

  5. Griffits, P.G., Sasse, J.M., Yokota, T., and Cameron, D.W., Biosci. Biotech. Biochem., 1995, vol. 59, p. 956.

    Article  Google Scholar 

  6. Kishi, T., Wada, K., Marumo, S., and Mori, K., Agric. Biol. Chem., 1986, vol. 50, p. 1821.

    CAS  Google Scholar 

  7. Takatsuto, S. and Ikekawa, N., J. Chem. Soc. Perkin Trans. 1, 1984, p. 439.

  8. Wada, K. and Marumo, S., Agric. Biol. Chem., 1981, vol. 45, p. 2579.

    CAS  Google Scholar 

  9. Khripach, V.A., Zhabinskii, V.N., and de Groot, A.E., Brassinosteroids: A New Class of Plant Hormones, San Diego: Academic, 1999.

    Google Scholar 

  10. Brassinosteroids: Steroidal Plant Hormones, Sakurai, A., Yokota, T., and Clouse, S.D., Eds., Tokyo: Springer, 1999.

    Google Scholar 

  11. Fujioka, S. and Yokota, T., Annu. Rev. Plant Biol., 2003, vol. 54, p. 137.

    Article  CAS  Google Scholar 

  12. Choi, Y.H., Fujioka, S., and Harada, A., Phytochemistry, 1996, vol. 43, p. 593.

    Article  CAS  Google Scholar 

  13. Watanabe, B., Yamamoto, S., Sasaki, K., Nakagawa, Y., and Miyagawa, H., Tetrahedron Lett., 2004, vol. 45, p. 2767.

    Article  CAS  Google Scholar 

  14. Watanabe, T., Noguchi, T., Yokota, T., Shibata, K., Koshino, H., Seto, H., Kim, S., and Takatsuto, S., Phytochemistry, 2001, vol. 58, p. 343.

    Article  CAS  Google Scholar 

  15. Mori, K., Sakakibara, M., and Okada, K., Tetrahedron, 1984, vol. 40, p. 1767.

    Article  CAS  Google Scholar 

  16. Baranovskii, A.V., Litvinovskaya, R.P., and Khripach, V.A., Bioorg. Khim., 2002, vol. 28, p. 277.

    CAS  Google Scholar 

  17. Huang-Minlon, J. Am. Chem. Soc., 1949, vol. 71, p. 3301.

    Article  CAS  Google Scholar 

  18. Thompson, M.J., Mandava, N., Flippen-Anderson, J.L., and Worley, J.F., J. Org. Chem., 1979, vol. 44, p. 5002.

    Article  CAS  Google Scholar 

  19. Anastasia, M., Ciuffreda, P., and Fiecchi, A., J. Chem. Soc., Perkin Trans. 1, 1983, p. 379.

  20. Khripach, V.A., Zhabinskii, V.N., Zhernosek, E.V., Lakhvich, F.A., Ol’khovik, V.K., and Ivanova, G.V., Vestsi Akad. Navuk BSSR, Ser. Khim. Navuk, 1991, no. 2, p. 271.

  21. Hellrung, B., Voigt, B., Schmidt, J., and Adam, G., Steroids, 1997, vol. 62, p. 415.

    Article  CAS  Google Scholar 

  22. Takatsuto, S., Watanabe, T., Fujioka, S., and Sakurai, A., J. Chem. Res., Synop., 1997, p. 134.

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Authors and Affiliations

  1. Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, ul. Akademika Kuprevicha 5/2, Minsk, 220141, Belarus

    R. P. Litvinovskaya, M. A. Aver’kova, A. V. Baranovskii & V. A. Khripach

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  1. R. P. Litvinovskaya
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  2. M. A. Aver’kova
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  3. A. V. Baranovskii
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  4. V. A. Khripach
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Original Russian Text © R.P. Litvinovskaya, M.A. Aver’kova, A.V. Baranovskii, V.A. Khripaeh, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 9, pp. 1344–1350.

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Litvinovskaya, R.P., Aver’kova, M.A., Baranovskii, A.V. et al. Synthesis of 6-deoxo-24-epiteasterone and its analogs. Russ J Org Chem 42, 1325–1332 (2006). https://doi.org/10.1134/S1070428006090120

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  • DOI: https://doi.org/10.1134/S1070428006090120

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