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Total Synthesis of Ellagitannins through Regioselective Sequential Functionalization of Unprotected Glucose
Author(s) -
Takeuchi Hironori,
Mishiro Kenji,
Ueda Yoshihiro,
Fujimori Yusuke,
Furuta Takumi,
Kawabata Takeo
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201500700
Subject(s) - regioselectivity , chemistry , surface modification , gallic acid , organic chemistry , derivative (finance) , glycosyl , glycoside , catalysis , combinatorial chemistry , financial economics , economics , antioxidant
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.