Journal
ORGANIC LETTERS
Volume 8, Issue 16, Pages 3609-3612Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol0614976
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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-(tertbutyldimethylsilyl) 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.
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