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A versatile synthesis of [2,3,4‐ 13 C 3 ]isoflavones
Author(s) -
AlMaharik Nawaf,
Botting Nigel P.
Publication year - 2010
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.1732
Subject(s) - formononetin , glycitein , chemistry , daidzein , biochanin a , isoflavones , genistein , equol , chalcone , stereochemistry , biochemistry , medicine
A flexible synthetic method is presented, which allows all the key isoflavones (daidzein, genistein, glycitein, formononetin and biochanin A) to be prepared in 13 C‐labelled form via the same route, involving the thallium(III)‐mediated oxidative rearrangement of a key chalcone intermediate. This method results in the incorporation of 13 C atoms at the 2, 3 and 4 positions of the isoflavone skeleton. We also report the first syntheses of 13 C‐labelled versions of the daidzein metabolites, equol and ODMA. Copyright © 2009 John Wiley & Sons, Ltd.