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化学学报
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化学学报 ›› 2008, Vol. 66 ›› Issue (9): 1129-1133. 上一篇    下一篇

研究简报

(20S)-20-羟基胆甾烷-3,16-二酮的合成

唐仕阳，张鲁中，任小娟，李瀛，谢志翔*   

  1. (兰州大学化学化工学院 功能有机分子国家重点实验室 兰州 730000)
  • 投稿日期:2007-11-01 修回日期:2007-12-20 发布日期:2008-05-14
  • 通讯作者: 谢志翔

The Synthesis of (20S)-20-Hydroxycholestane-3,16-Dione

TANG Shi-Yang ZHANG Lu-Zhong REN Xiao-Juan LI Ying XIE Zhi-Xiang*   

  1. (State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000)
  • Received:2007-11-01 Revised:2007-12-20 Published:2008-05-14
  • Contact: XIE Zhi-Xiang

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以妊娠双烯醇酮醋酸酯为起始原料, 经过7步反应以13.1%的总收率合成了一个具有抗4种肿瘤细胞(ED50＝1 μg/mL)的海洋天然产物(20S)-20-羟基胆甾烷-3,16-二酮. 关键反应为底物控制的不对称杂原子共轭加成反应.

关键词: 胆甾烷, 抗肿瘤, 杂原子共轭加成, 欧芬脑尔氧化, 伯奇还原

The synthesis of (20S)-20-hydroxycholestane-3,16-dione, a marine natural product against four tumor cell lines (ED50＝1 μg/mL), was achieved from 16-dehydropregnenolone acetate in seven steps with a 13.1% overall yield. The key step was a substrate controlled asymmetric heteroatom conjugated addition.

Key words: cholestane, antitumor, heteroatom conjugated addition, Oppennauer oxidation, Birch reduction