title: Total Synthesis of Ellagitannins through Regioselective Sequential Functionalization of Unprotected Glucose.
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.
authors: Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan).
authors: Hironori
authors: H
authors: Takeuchi
authors: Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan).
authors: Kenji
authors: K
authors: Mishiro
authors: Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan).
authors: Yoshihiro
authors: Y
authors: Ueda
authors: Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan).
authors: Yusuke
authors: Y
authors: Fujimori
authors: Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan).
authors: Takumi
authors: T
authors: Furuta
authors: Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan). kawabata@scl.kyoto-u.ac.jp.
authors: Takeo
authors: T
authors: Kawabata
mesh_terms: D005707:Gallic Acid / Q000138:chemical synthesis / Q000737:chemistry; D005947:Glucose / Q000138:chemical synthesis / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry; D006031:Glycosylation; D047348:Hydrolyzable Tannins / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D006027:Glycosides; D047348:Hydrolyzable Tannins; D005707:Gallic Acid; D005947:Glucose
keywords: ellagitannin; glycosidation; organocatalysis; regioselectivity; total synthesis