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化学进展 2012, Vol. Issue (9): 1742-1750 前一篇   后一篇

• 综述与评论 •

倍半萜EnglerinA及其类似物的合成

乐贵洲*, 黄乾明, 邹平   

  1. 四川农业大学生命科学与理学院 雅安 625014
  • 收稿日期:2011-12-01 修回日期:2012-03-01 出版日期:2012-09-24 发布日期:2012-09-27
  • 通讯作者: 乐贵洲 E-mail:yueguizhou@sicau.edu.cn
  • 基金资助:

    四川省教育厅重点项目(No.00724900)及四川农业大学双支计划(No.00770104)资助

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Synthesis of Sesquiterpenoids: Englerin A and Its Analogues

Yue Guizhou, Huang Qianming, Zou Ping   

  1. College of Biology and Science, Sichuan Agricultural University, Ya'an 625014, China
  • Received:2011-12-01 Revised:2012-03-01 Online:2012-09-24 Published:2012-09-27
2008年从东非大戟科属植物Phyllanthus engleri 中分离的吉玛烷型倍半萜(-)-englerin A对6种肾脏癌细胞展示了非常好的抑制活性(GI50:1-87nm),甚至比紫杉醇的抗癌活性高1-2个数量级。这类倍半萜因其结构特点和显著的抗癌活性引起了有机化学界的广泛关注, 短短几年之内,就有多条全合成路线先后被报道。本文主要综述了(-)-englerin A及其类似物的合成进展,按照各个研究小组运用的关键策略加以分类,来阐述他们各自的合成特点。
关键词： 倍半萜, (-)-englerin, A, 合成
In 2008, the guaiane sesquiterpene (-)-englerin A, isolated from the genus phyllanthus engleri in East Africa, selectively inhibited the growth of renal cancer cell lines with GI50 values ranging from 1—87nm. It was found to be 1—2 orders of magnitude more potent than taxol against certain cell lines. The promising bioactivity and the structural complexity of (-)-englerin A and its analogues have attracted many organic chemists all over the world. Many studies toward the total synthesis of englerin A and its analogues were reported in three years. The article reviews the progress on the synthesis of englerin A and its analogues,We classified these syntheses according to key strategies for syntheses of englerin A and its analogues and elaboratted the characteristics of these synthetic routes. Contents 1 Introduction
2 Key strategies for syntheses of englerin A and its analogues
2.1 Ring-closing metathesis (RCM)
2.2 Gold(Ⅰ)-catalytic domino reaction
2.3 Oxopyrilium [5+2] cycloaddition
2.4 Rh(Ⅱ)-catalytic [4+3] cycloaddition
2.5 Organocatalytic [4+3] cycloaddition
2.6 Transannular epoxide opening reaction
2.7 SmI2-mediated cyclization
3 Conclusions and outlook
Key words: sesquiterpenoids, (-)-englerin A, synthesis

中图分类号: 

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摘要

倍半萜EnglerinA及其类似物的合成