Novel and efficient synthesis of cyanidin 3-O-beta-D-glucoside from (+)-catechin via a flav-3-en-3-ol as a key intermediate.
[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.
Kondo
Tadao
T
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.
Oyama
Kin-Ichi
K
Nakamura
Saki
S
Yamakawa
Daisuke
D
Tokuno
Kazunari
K
Yoshida
Kumi
K
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
D000872:Anthocyanins; D005960:Glucosides; C462279:cyanidin-3-O-beta-glucopyranoside; D002392:Catechin