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Acta Chimica Sinica ›› 2007, Vol. 65 ›› Issue (20): 2315-2319. Previous Articles     Next Articles

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

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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