Synthesis of 14伪-substituted androstanes鈥擪ey compounds in the synthesis of 14-substituted brassinosteroids

详细信息    查看全文

• 作者：A. V. Baranovskii (1)
  D. A. Bolibrukh (1)
  B. Schneider (2)
  
  1. Institute of Bioorganic Chemistry ; National Academy of Sciences of Belarus ; ul. Akademika Kuprevicha 5/2 ; Minsk ; 220141 ; Belarus
  2. Max Planck Institute for Chemical Ecology ; Beutenberg Campus ; Hans Kn枚ll Str. 8 ; D-07745 ; Jena ; Germany
  
• 刊名：Russian Journal of Organic Chemistry
• 出版年：2015
• 出版时间：January 2015
• 年：2015
• 卷：51
• 期：1
• 页码：78-85
• 全文大小：277 KB
• 参考文献：1. Baranovskii, A.V. and Khripach, V.A., / Russ. J. Gen. Chem., 2011, vol. 81, p. 2142. CrossRef
  2. Baranovsky, A.V., Bolibrukh, D.A., Khripach, V.A., and Schneider, B., / Steroids, 2013, vol. 78, p. 282. CrossRef
  3. Bull, J.R. and Thomson, R.I., / J. Chem. Soc., Chem. Commun., 1986, p. 451.
  4. Bull, J.R. and Steer, L.M., / Tetrahedron, 1990, vol. 46, p. 5401. CrossRef
  5. Bull, J.R. and Steer, L.M., / Tetrahedron, 1991, vol. 47, p. 7377. CrossRef
  6. Bull, J.R. and Thomson, R.I., / J. Chem. Soc., Perkin Trans. 1, 1990, p. 241.
  7. Armesto, D., Horspool, W.M., Gallego, M.G., and Agarrabeitia, A.R., / J. Chem. Soc., Perkin Trans. 1, 1992, p. 163.
  8. Kikuchi, H., Okazaki, K., Sekiya, M., Uryu, Y., Ueda, K., Katou, Y., Kurata, S., and Oshima, Y., / Eur. J. Med. Chem., 2011, vol. 46, p. 1263. CrossRef
  9. Wadsworth, W.S. and Emmons, W.D., / Org. Synth., 1964, vol. 45, p. 44.
  10. Armarego, W.L.F. and Chai, C.L.L., / Purification of Laboratory Chemicals, Amsterdam: Butterworth-Heinemann, 2003, 5th ed.
  
• 刊物主题：Organic Chemistry;
• 出版者：Springer US
• ISSN：1608-3393

文摘

Ethyl 3-(6,6-ethylenedioxy-2伪,3伪-isopropylidenedioxy-17-oxo-5伪-androstan-14伪-yl)propanoate, the key intermediate product in the synthesis of brassinosteroids modified in the D ring, was synthesized from 6,6-ethylenedioxy-2伪,3伪-isopropylidenedioxy-5伪-androsta-14,16-dien-17-yl acetate via reaction sequence including Diels-Alder cycloaddition with phenyl vinyl sulfone, dihydroxylation, Malaprade diol cleavage, and selective Horner-Wadsworth-Emmons olefination.