高等学校化学学报

高等学校化学学报 ›› 2013, Vol. 34 ›› Issue (8): 1858.doi: 10.7503/cjcu20130279

• 有机化学 • 上一篇    下一篇

白屈菜红碱的全合成

黄康伦, 谢龙观, 吕培, 郭翠, 徐效华   

  1. 南开大学元素有机化学国家重点实验室, 元素有机化学研究所, 天津 300071
  • 收稿日期:2013-03-26 出版日期:2013-08-10 发布日期:2013-07-19
  • 通讯作者: 谢龙观,女,讲师,主要从事农药化学领域的研究.E-mail:xielg@syn.nankai.edu.cn E-mail:xielg@syn.nankai.edu.cn
  • 基金资助:

    国家科技支撑计划项目(批准号: 2011BAE06B05)资助.

Total Synthesis of Chelerythrine

HUANG Kang-Lun, XIE Long-Guan, LÜ Pei, GUO Cui, XU Xiao-Hua   

  1. State Key Laboratory of Elemento-organic Chemistry, Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China
  • Received:2013-03-26 Online:2013-08-10 Published:2013-07-19
  • Contact: LongGuan Xie E-mail:xielg@syn.nankai.edu.cn

PDF (PC)

被引次数

2

摘要：

以2,3-二甲氧基-6-溴苄醇(1)为起始原料, 经过6步反应合成关键中间体2,3-二甲氧基-6-碘苯甲酸甲酯(7), 通过金属钯催化下与中间体(8)的串联反应策略一步构筑了白屈菜红碱的B/C环, 并以10步60.9%的总收率完成了白屈菜红碱的全合成, 同时对关键的金属钯催化串联反应机理进行了初步探讨, 为高效合成苯并[c]菲啶类生物碱提供了一条简便路线.

关键词: 苯并[c]菲啶, 白屈菜红碱, 全合成

Abstract:

Chelerythrine is an isoquinoline alkaloid isolated from Herba Chelidonii that possess complex structure and remarkable activities. In this work, its total synthetic approach was investigated. Key meditate methyl 6-iodo-2,3-dimethoxybenzoate(7) was obtained in six steps with(6-bromo-2,3-dimethoxyphenyl)methanol(1) as starting material. The core structure was efficiently constructed by palladium-catalyzed tandem reaction in one step. At the same time, a proposed mechanism of palladium-catalyzed tandem reaction was suggested and the chelerythrine was synthesized in 10 steps with a total yield of 60.9%. All compounds were confirmed by IR, 1H NMR, 13C NMR and high resolution mass spectrometer(HRMS).

Key words: Benzo[c]phenanthridine, Chelerythrine, Total synthesis

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