Enantioselective Total Synthesis of (-)-Incarviatone A

被引:66
|
作者
Hong, Benke [1 ,2 ,3 ]
Li, Chao [1 ,2 ]
Wang, Zhen [4 ]
Chen, Jie [3 ]
Li, Houhua [4 ]
Lei, Xiaoguang [1 ,2 ,4 ]
机构
[1] Peking Univ, Beijing Natl Lab Mol Sci, Dept Biol Chem, Coll Chem & Mol Engn,Synthet & Funct Biomol Ctr, Beijing 100871, Peoples R China
[2] Peking Univ, PekingTsinghua Ctr Life Sci, Beijing 100871, Peoples R China
[3] Tianjin Univ, Sch Pharmaceut Sci & Technol, Tianjin 300072, Peoples R China
[4] NIBS, Beijing 102206, Peoples R China
关键词
C-H FUNCTIONALIZATION; BIOMIMETIC TOTAL-SYNTHESIS; BOND FUNCTIONALIZATION; NATURAL-PRODUCTS; CONCISE SYNTHESES; INSERTION; STRATEGY; CONFIGURATION; CONSTRUCTION; DERIVATIVES;
D O I
10.1021/jacs.5b08551
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report herein the first total synthesis of (-)-incarviatone A (1) in 14 steps starting from commercially available inexpensive phenylacetic acid (9). Our early stage synthesis relies on the scalable and sequential C-H functionalitation to rapidly assemble the indanyl dialdehyde framework. Further biomimetic cascade strategy allows us to obtain the natural product in a onepot operation. We also conduct detailed mechanistic studies and disclose all the possible intermediates and isomers formed during the biomimetic cascade process.
引用
收藏
页码:11946 / 11949
页数:4
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