有机化学 ›› 2010, Vol. 30 ›› Issue (9): 1305-1313. 上一篇    下一篇

综述与进展

单萜吲哚生物碱Alstonerine的合成研究进展

周华凤1,2,刘建利*,1,王翠玲1   

  1. (1西北大学生命科学院 西部资源生物与现代生物技术省部共建教育部重点实验室 西安 710069)
    (2西安建筑科技大学化学系 西安 710055)
  • 收稿日期:2009-12-17 修回日期:2010-03-27 发布日期:2010-05-27
  • 通讯作者: 周华凤 E-mail:xianghuihf115@163.com
  • 基金资助:

    以仿生合成策略设计合成钩藤中的单萜吲哚生物碱,;中医气与NO相关性的实验与临床研究

Progress of Synthetic Study of Monoterpenoid Indole Alkaloid Alston-erine

Zhou Huafeng1,2 Liu Jianli*,1 Wang Cuil-ing1   

  1. (1 Key Laboratory of Resource Biology and Biotechnology in Western China, Ministry of Educa-tion, School of Life Science, Northwest University, Xi an 710069)
    (2 Department of Chemistry, Xi an University of Architecture and Technology, Xi an 710055)
  • Received:2009-12-17 Revised:2010-03-27 Published:2010-05-27
  • Contact: zhou hua feng E-mail:xianghuihf115@163.com

Alstonerine属于单萜吲哚生物碱, 除其结构很有特征外, 还报道对两株人肺癌细胞具有细胞毒性, 因此, 它自然就成为合成化学的重要目标. 已经有多种合成策略用于构建这个结构体系: 包括Pictet-Spengler反应和Dieckmann 缩合反应、烯烃复分解关环反应、膦配体催化的[4+2]关环/Friedel-Craft环化、氮杂-Diels-Alder反应/分子内 Heck 反应、Pauson-Khand反应等. 本工作根据构建环系的不同反应系统总结了Alstonerine的合成方法. 大部分合成反应步骤较多, 适合工业生产的有效合成方法还有待于进一步探索.

关键词: Alstonerine, 合成, 仿生合成

In addition to its challenging structural features, alstonerine, as a representative member of the macroline family of alkaloids, has been reported to exhibit cytotoxic activity against two human lung cancer cell lines, so it has been the subject of a number of synthetic studies. Several strategies have been devised to access this structural motif including a sequential Pictet-Spengler reaction and Dieckmann condensation, ring-closing metathesis, phosphine-catalyzed [4+2] annulation/Friedel-Crafts cyclization, aza-Diels-Alder/ intramolecular Heck reaction, Pauson-Khand reaction. In this paper, the synthetic methods are reviewed ac-cording to the key building reactions of the ring structures. Most routes to alstonerine are through complicated steps. Hence, the simple and convenient methods are still needed to further study.

Key words: Alstonerine, synthesis, biomimetic synthesis