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13 C‐Labelled (±±)‐Catechin From Potassium [ 13 C]Cyanide
Author(s) -
Nay Bastien,
Arnaudinaud Valérie,
Peyrat JeanFrançois,
Nuhrich Alain,
Deffieux Gérard,
Mérillon JeanMichel,
Vercauteren Joseph
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200004)2000:7<1279::aid-ejoc1279>3.0.co;2-d
Subject(s) - chemistry , phloroglucinol , potassium cyanide , chalcone , catechin , organic chemistry , trifluoroacetic anhydride , synthon , polyphenol , acylation , potassium , caffeic acid , trifluoroacetic acid , cyanide , stereochemistry , catalysis , antioxidant
Racemic 4‐[ 13 C]catechin 14 has been synthesized in ten steps starting from potassium [ 13 C]cyanide. The intermediate chalcone 9 was formed by acylation of the benzylated phloroglucinol 7 with the caffeic acid synthon 6 , using the trifluoroacetic mixed anhydride. The flavonoid skeleton was then obtained by previously described reactions such as the reduction of chalcone 9 and dihydroxylation of flavene 11 . Such [ 13 C]‐labelled polyphenols should prove to be useful tools for human biological investigations.