通过可见光催化直接合成双环缩醛
Direct Synthesis of Bicyclic Acetals via Visible Light Catalysis.
作者信息
Wu Fengjin, Wang Leifeng, Ji Ying, Zou Ge, Shen Hong, Nicewicz David A, Chen Jiean, Huang Yong
机构信息
State Key Laboratory of Chemical Oncogenomics, Key Laboratory of Chemical Genomics, Peking University, Shenzhen Graduate School, Shenzhen 518055, China.
State Key Laboratory of Chemical Oncogenomics, Key Laboratory of Chemical Genomics, Peking University, Shenzhen Graduate School, Shenzhen 518055, China; Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290, USA.
出版信息
iScience. 2020 Aug 21;23(8):101395. doi: 10.1016/j.isci.2020.101395. Epub 2020 Jul 24.
Polysubstituted bicyclic acetals are a class of privileged pharmacophores with a unique 3D structure and an adjacent pair of hydrogen bond acceptors. The key, fused acetal functionality is often assembled, via intramolecular cyclization, from linear substrates that are not readily available. Herein, we report a formal cycloaddition between cinnamyl alcohols and cyclic enol ethers under ambient photoredox catalysis conditions. Polysubstituted bicyclic acetals can be prepared in one step from readily available building blocks. Employment of sugar-derived enol ethers allows easy access to a library of scaffolds with intriguing conformation and medicinal chemistry potential.
多取代双环缩醛是一类具有独特三维结构和相邻氢键受体对的优势药效基团。关键的稠合缩醛官能团通常通过分子内环化，从不易获得的线性底物组装而成。在此，我们报道了在环境光氧化还原催化条件下肉桂醇与环状烯醇醚之间的形式环加成反应。多取代双环缩醛可以从容易获得的构建块一步制备。使用糖衍生的烯醇醚可以方便地获得一系列具有有趣构象和药物化学潜力的支架。
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