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Total Synthesis of Ellagitannins through Regioselective Sequential Functionalization of Unprotected Glucose
Hironori Takeuchi1, Kenji Mishiro1, Yoshihiro Ueda1
1Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan).
Abstract:
Short total syntheses of natural glycosides (ellagitannins) were performed through sequential and regioselective functionalization of the hydroxy groups of unprotected glucose. The key reactions are β-selective glycosidation of a gallic acid derivative by using unprotected glucose as a glycosyl donor and catalyst-controlled regioselective introduction of a galloyl group into the inherently less reactive hydroxy group of the glucoside.
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