title: Total Synthesis of Ellagitannins via Sequential Site-Selective Functionalization of Unprotected D-Glucose.
abstract: A short-step total synthesis of the natural glycosides pterocarinin C and tellimagrandin II (eugeniin) has been performed by sequential and site-selective functionalization of free hydroxy groups of unprotected D-glucose. The key reactions are β-selective glycosidation of a gallic acid derivative using unprotected D-glucose as a glycosyl donor and catalyst-controlled site-selective introduction of a galloyl group into the inherently less reactive hydroxy group of the glucoside.
authors.affiliation: Institute for Chemical Research, Kyoto University.
authors.forename: Hironori
authors.initials: H
authors.lastname: Takeuchi
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Ueda
authors.forename: Takumi
authors.initials: T
authors.lastname: Furuta
authors.forename: Takeo
authors.initials: T
authors.lastname: Kawabata
mesh_terms: D005947:Glucose / Q000737:chemistry*; D047348:Hydrolyzable Tannins / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D047348:Hydrolyzable Tannins; C013515:ellagitannin; D005947:Glucose