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Chin. J. Org. Chem. ›› 2007, Vol. 27 ›› Issue (9): 1142-1146. Previous Articles     Next Articles

Original Articles

多羟基甾醇25(R)-异螺甾环-5-烯-2β,3α,19-三醇的合成

金志敏a，张静夏*,b，罗美凤b，冷田东c
黄亦俊c，颜光美c 王红英a   

  1. (a郑州大学材料科学与工程学院 郑州 450001)
    (b中山大学药学院 广州 510089)
    (c中山大学中山医学院 广州 510089)
  • 收稿日期:2006-11-06 修回日期:2007-02-01 发布日期:2007-08-30
  • 通讯作者: 张静夏

Synthesis of Polyhydroxy Sterol 25(R)-Isospirost-5-en-2β,3α,19-triol

JIN Zhi-Mina,ZhANG Jing-Xia*,b,LUO Mei-Fengb,LENG Tian-Dongc
HUANG Yi-Junc,YAN Guang-Meic,WANG Hong-Yinga   

  1. (a School of Material Science and Engineering, Zhengzhou University, Zhengzhou 450001)
    (b School of Pharmacetical Sciences, Sun Yat-sen University, Guangzhou 510089)
    (c Zhongshan School of Medicine, Sun Yat-sen Univer-sity, Guangzhou 510089)
  • Received:2006-11-06 Revised:2007-02-01 Published:2007-08-30
  • Contact: ZhANG Jing-Xia

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The polyhydroxy sterol 25(R)-isospirost-5-en-2β,3α,19-triol was synthesized from diosgenin by seven steps including tosylation, oxidative addition with N-bromo-succinimide (NBS), far-way oxidation with Pb(OAc)4, elimination, oxidation of m-chloroperbenzonic acid (mCPBA) and reduction with Zn powder. The structures of the intermediates and the target product were elucidated by IR, 1H NMR, 13C NMR, MS spectra and elemental analysis.

Key words: 25(R)-isospirost-5-en-2β,3α,19-triol, polyhydroxy sterol, diosgenin