Citation: Jin Wenbing, Yuan Hua, Tang Gongli. Strategies for Construction of Cyclopropanes in Natural Products[J]. Chinese Journal of Organic Chemistry, ;2018, 38(9): 2324-2334. doi: 10.6023/cjoc201805059 shu

Strategies for Construction of Cyclopropanes in Natural Products

State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Corresponding author: Tang Gongli, gltang@sioc.ac.cn
Received Date: 31 May 2018
Revised Date: 26 June 2018
Available Online: 24 September 2018
Fund Project: the Science and Technology Commission of Shanghai Municipality 15ZR1449400Project supported by the National Natural Science Foundation of China (No. 21502217) and the Science and Technology Commission of Shanghai Municipality (No. 15ZR1449400)the National Natural Science Foundation of China 21502217

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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 S_N2 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.
- natural products,
- cyclopropane,
- chemical synthesis,
- biosynthesis,
- catalytic mechanism
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