Lewis Acid-Catalyzed Tandem Annulation of Propargylic Alcohols with 2-Allylphenols and Their Anti-tumor Activities

文献类型： 外文期刊

第一作者： Li, Xiang

作者： Li, Xiang;Guo, Ning-Yu;Liu, Qing-Hui;Han, Ya-Ping;Zhang, Hong-Yu;Peng, Li-Zeng

作者机构：

关键词： Lewis acid-catalyzed; Propargylic alcohols; 2-Allylphenols; Meyer-Schuster rearrangement; Anti-tumor activities

期刊名称：ASIAN JOURNAL OF ORGANIC CHEMISTRY （ 影响因子：2.8； 五年影响因子：2.8 ）

ISSN： 2193-5807

年卷期： 2024 年

页码：

收录情况： SCI

摘要： A novel bismuth(III) trifluoro-methanesulfonate-catalyzed and environmentally benign synthetic strategy for the construction of a wide range of structurally diverse, sophisticated [5,6,5]-oxygen-containing tricyclic frameworks with easy-to handle propargylic alcohols and 2-allylphenols as substrates in the presence of Bi(OTf)3 and AgOTf is described. This Lewis acid catalyzed [3+2] annulation protocol, which tolerates a great deal of functional groups, proceeds through a sequential Meyer-Schuster rearrangement, nucleophilic substitution, 5-exo-trig cyclization, 5-endo-trig cyclization, and proton exchange sequences, affording a versatile approach for accessing oxygen-containing tricyclic skeletons in moderate-to-excellent yields. In addition, most of the obtained compounds exhibited anti-tumor activities against three types of human cancer cell lines in vitro, including Caco-2 colon cancer cells, MCF-7 breast cancer cells, and Hepg-2 liver cancer cells. A novel strategy for the assembly of a wide range of structurally diverse, sophisticated [5,6,5]-oxygen-containing tricyclic frameworks is developed through bismuth(III) trifluoro-methanesulfonate-catalyzed [3+2] annulation protocol. Moderate-to-excellent yields are observed among different propargylic alcohols and 2-allylphenols, providing a practical approach for accessing oxygen-containing tricyclic skeletons, which exhibit anti-tumor activities against three types of human cancer cell lines. image

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