Acta Chimica Sinica ›› 2008, Vol. 66 ›› Issue (9): 1129-1133. Previous Articles     Next Articles

Reports

(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

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