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Rapid construction of the ABD tricyclic skeleton in meliacarpinin B from carvone enabled by an INOC strategy
Organic Chemistry Frontiers ( IF 5.4 ) Pub Date : 2020-06-17 , DOI: 10.1039/d0qo00576b
Changming Dong 1, 2, 3, 4 , Tianjiao Qiao 1, 2, 3, 4 , Yi Xie 1, 2, 3, 4 , Xiao Zhang 1, 2, 3, 4 , Junli Ao 1, 2, 3, 4 , Guangxin Liang 4, 5, 6, 7
Affiliation  

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.

中文翻译:

通过INOC策略可从香芹酮中快速构建木瓜蛋白酶B中的ABD三环骨架

提出了麦考卡丁B的ABD骨架的高度非对映选择性合成。关键的反式十氢化萘单元的构建具有在易于获得的香芹酮衍生物上的分子内腈氧化烯-烯烃环加成(INOC)反应的特征。该策略使得能够从R-香芹酮以14个简单的线性步骤制备具有6个连续的立体异构中心的三环核心。
更新日期:2020-07-14
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