Journal Article Total Synthesis of Ellagitannins through Regioselective Sequential Functionalization of Unprotected Glucose.

Takeuchi, Hironori  ,  Mishiro, Kenji  ,  Ueda, Yoshihiro  ,  Fujimori, Yusuke  ,  Furuta, Takumi  ,  Kawabata, Takeo

54 ( 21 )  , pp.6177 - 6180 , 2015-05-18 , wiley
Article first published online: 9 APR 2015
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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