An Approach to the Synthesis of Electron-Rich and Hindered Esters and Its Application to the Synthesis of Acteoside
Xiaojuan Zhang, Yutong Yang, Fuye Wang, Zhengbing Zhou, Hongbin Zhang, Yugen Zhu
Abstract
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.
Topics & Concepts
ChemistryPhenylethanoidAcylationCombinatorial chemistryAlkyneGlycosideCatalysisOrganic chemistryTraditional and Medicinal Uses of AnnonaceaeMarine Sponges and Natural ProductsPhytochemical compounds biological activities