An Approach to the Synthesis of Electron-Rich and Hindered Esters and Its Application to the Synthesis of Acteoside.
An Approach to the Synthesis of Electron-Rich and Hindered Esters and Its Application to the Synthesis of Acteoside.
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DOI：
10.1021/acs.orglett.1c03528
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发表时间：
2021-11
期刊：
影响因子：
5.2
通讯作者：
Xiaojuan Zhang;Yutong Yang;Fuye Wang;Zhengbing Zhou;Hongbin Zhang;Yugen Zhu
中科院分区：
文献类型：
--
作者：
Xiaojuan Zhang;Yutong Yang;Fuye Wang;Zhengbing Zhou;Hongbin Zhang;Yugen Zhu
富电子酯类化合物普遍存在于天然产物中，在生物活性中起着重要作用。在此，我们揭示了一种高效、温和、通用的酯化方法，通过金(I)催化与炔系混合酸酐和醇的酰化反应来合成这些酯。该方法可应用于复杂底物的酯键形成，促进了毛蕊花苷的高效合成。毛蕊花苷属于苯乙醇苷家族，具有广泛的生物活性。
Electron-rich esters are ubiquitously distributed in natural products and play a central role in bioactivities. Herein, we disclose an efficient, mild, and general esterification approach to the synthesis of these esters by employing gold(I)-catalyzed acylation reaction with alkyne-tethered mixed anhydrides and alcohols. This method can be applied to ester-bond formation in complex substrates and facilitates efficient synthesis of acteoside, which belongs to the family of phenylethanoid glycosides and possesses a broad range of bioactivities.