title: Novel and efficient synthesis of cyanidin 3-O-beta-D-glucoside from (+)-catechin via a flav-3-en-3-ol as a key intermediate.
abstract: [reaction: see text] A novel and efficient synthesis of cyanidin 3-O-beta-D-glucoside (1) was accomplished the first time by a biomimetic oxidation route. From (+)-catechin, 3-OH was glucosylated, and the 4-position of the nucleus was then oxidized and dehydrated to give the 5,7,3',4'-tetra-O-(tert-butyldimethylsilyl)flav-3-en-3-ol 3-O-glucoside (8) as a key intermediate. 8 was deprotected and oxidized under air in hydrogen chloride-MeOH to give 1.
authors.affiliation: Graduate School of Information Science, Chemical Instrument Room, Research Center for Materials Science, Graduate School of Bioagricultural Sciences, and Graduate School of Human Informatics, Nagoya University, Chikusa, Nagoya 464-8601, Japan.
authors.forename: Tadao
authors.initials: T
authors.lastname: Kondo
authors.forename: Kin-Ichi
authors.initials: K
authors.lastname: Oyama
authors.forename: Saki
authors.initials: S
authors.lastname: Nakamura
authors.forename: Daisuke
authors.initials: D
authors.lastname: Yamakawa
authors.forename: Kazunari
authors.initials: K
authors.lastname: Tokuno
authors.forename: Kumi
authors.initials: K
authors.lastname: Yoshida
mesh_terms: D000872:Anthocyanins / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002392:Catechin / Q000737:chemistry*; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000872:Anthocyanins; D005960:Glucosides; C462279:cyanidin-3-O-beta-glucopyranoside; D002392:Catechin