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A versatile synthesis of [2,3,4-13C3]isoflavones

✍ Scribed by Nawaf Al-Maharik; Nigel P. Botting

Publisher
John Wiley and Sons
Year
2010
Tongue
French
Weight
207 KB
Volume
53
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

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.

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