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有机化学 ›› 2007, Vol. 27 ›› Issue (9): 1142-1146. 上一篇    下一篇

研究论文

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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以薯蓣皂素为原料, 经过磺酰酯化、N-溴代丁二酰亚胺(NBS)氧化加成、Pb(OAc)4远程氧化关环、消去反应、间氯过氧苯甲酸(mCPBA)氧化、高氯酸开环及锌粉还原7步反应, 合成多羟基甾体25(R)-异螺甾环-5-烯-2β,3α,19-三醇. 并用IR, 1H NMR, 13C NMR, MS及元素分析对各中间体及目标化合物进行了表征.

关键词: 薯蓣皂素, 多羟基甾醇, 25(R)-异螺甾环-5-烯-2β,3α,19-三醇

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