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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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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.[1]

References

  1. Novel and efficient synthesis of cyanidin 3-O-beta-D-glucoside from (+)-catechin via a flav-3-en-3-ol as a key intermediate. Kondo, T., Oyama, K., Nakamura, S., Yamakawa, D., Tokuno, K., Yoshida, K. Org. Lett. (2006) [Pubmed]
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