Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (9): 2324-2334.DOI: 10.6023/cjoc201805059 Previous Articles     Next Articles

Special Issue: 合成科学

Reviews

天然产物中环丙烷官能团的构筑策略

金文兵, 袁华, 唐功利   

  1. 中国科学院上海有机化学研究所 生命有机化学国家重点实验室 上海 200032
  • 收稿日期:2018-05-31 修回日期:2018-06-26 出版日期:2018-09-25 发布日期:2018-07-24
  • 通讯作者: 唐功利 E-mail:gltang@sioc.ac.cn
  • 基金资助:

    国家自然科学基金(No.21502217)和上海市自然科学基金(No.15ZR1449400)资助项目.

Strategies for Construction of Cyclopropanes in Natural Products

Jin Wenbing, Yuan Hua, Tang Gongli   

  1. State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
  • Received:2018-05-31 Revised:2018-06-26 Online:2018-09-25 Published:2018-07-24
  • Contact: 10.6023/cjoc201805059 E-mail:gltang@sioc.ac.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21502217) and the Science and Technology Commission of Shanghai Municipality (No. 15ZR1449400).

Cyclopropane-containing natural products frequently possess excellent biological activities, and may be developed as drug leads. Although the inherent strain of the cyclopropane greatly challenges both chemical synthesis and biosynthesis, great advances have been made for the construction of the cyclopropane in natural products by chemical synthesis owing to the importance of this kind of compounds. Many enzymes responsible for cyclopropanation have also been unraveled. This review summarizes the cyclopropanation strategies in chemical synthesis and biosynthesis. The strategies used in chemical synthesis mainly consist of three classes:(i) a carbene involved mechanism, (ii) an SN2 reaction mechanism, and (iii) cycloisomerization. The strategies discovered in nature are reviewed on the basis of the carbon state involved, including (i) a carbocation, (ii) a carbanion, and (iii) a carbon radical. Chemical synthesis and biosynthesis are mutually simulative because the strategies developed in chemical synthesis may inspire enzymologists to discover and design new biochemical reactions and vice versa.

Key words: natural products, cyclopropane, chemical synthesis, biosynthesis, catalytic mechanism