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化学学报
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化学学报 ›› 2007, Vol. 65 ›› Issue (20): 2315-2319. 上一篇    下一篇

研究论文

利用薯蓣皂甙元完整骨架合成澳洲茄胺

唐小枚1，许启海2，王静1，林静容*,1，金荣华1，田伟生*,1,2   

  1. (1上海师范大学资源化学实验室 上海 200234)
    (2中国科学院上海有机化学研究所 上海 200032)
  • 投稿日期:2007-04-06 修回日期:2007-05-23 发布日期:2007-10-28
  • 通讯作者: 田伟生

Synthesis of Solasodine by Using the Intact Skeleton of Diosgenin

TANG Xiao-Mei1; XU Qi-Hai2; WANG Jing1; LIN Jing-Rong*,1; JIN Rong-Hua1; TIAN Wei-Sheng*,1,2   

  1. (1 The Laboratory of Resource Chemistry, Shanghai Normal University, Shanghai 200234)
    (2 Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032)
  • Received:2007-04-06 Revised:2007-05-23 Published:2007-10-28
  • Contact: TIAN Wei-Sheng

PDF

771

被引次数

48

澳洲茄胺1是中药龙葵生物活性成分澳洲茄碱和澳洲茄边碱的甙元, 具有抗肿瘤等生物活性. 利用薯蓣皂甙元的完整骨架, 以16-羟基甾体皂甙元的溴代开环反应为关键反应, 经9步反应, 以21%的总收率完成了澳洲茄胺1的合成.

关键词: 澳洲茄胺, 薯蓣皂甙元, 甾体生物碱, 龙葵

Solasodine 1, the aglycon of solasonine and solamargine with the antitumour activity isolated from Chinese medicinal herb “Long Kui” Solalum nigrum l., was synthesized by utilizing the intact skeleton of diosgenin in 9 steps and in 21% overall yield. The key reaction in the synthesis involved a new bromination-E/F ring-opening reaction of 16-hydroxy-steroidal sapogenins.

Key words: Solasodine, diosgenin, steroidal alkaline; Solalum Nigrum L