Rapid construction of the ABD tricyclic skeleton in meliacarpinin B from carvone enabled by an INOC strategy
文献信息
发布日期
2020-06-17
DOI
10.1039/D0QO00576B
影响因子
5.281
作者
Changming Dong, Tianjiao Qiao, Yi Xie, Xiao Zhang, Junli Ao, Guangxin Liang
查看原文
摘要
A highly diastereoselective synthesis of the ABD skeleton of meliacarpinin B is presented. The construction of the key trans-decalin unit features an intramolecular nitrile oxide-alkene cycloaddtion (INOC) reaction on a readily available carvone derivative. This strategy enabled prepration of the tricyclic core bearing 6 contiguous stereogenic centres in 14 straightforward linear steps from R-carvone.
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来源期刊
Organic Chemistry Frontiers
CiteScore:
7.8
自引率:
8.7%
年发文量:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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485799-04-0
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C15H23BN2O3
![N-[(1S,2R,4S)-2-Amino-4-(dimethylcarbamoyl)cyclohexyl]-N'-(5-chloro-2-pyridinyl)ethanediamide structure](https://cnstatic.chemtradehub.com/structs/480/480452-37-7-0898.webp "N-[(1S,2R,4S)-2-Amino-4-(dimethylcarbamoyl)cyclohexyl]-N'-(5-chloro-2-pyridinyl)ethanediamide structure")
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