||Total Synthesis of Ellagitannins through Regioselective Sequential Functionalization of Unprotected Glucose.
Takeuchi, Hironori ,
Mishiro, Kenji ,
Ueda, Yoshihiro ,
Fujimori, Yusuke ,
Furuta, TakumiKawabata, Takeo
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.