The synthesis of [2,3,4-C-13(3)]glycitein

Q Z Zhang, N P Botting

Research output: Contribution to journalArticlepeer-review

23 Citations (Scopus)

Abstract

Glycitein is one of the soy isoflavones which have attracted considerable interest in recent years due to their possible beneficial effects on human health. However, glycitein has been much less studied than other members of this family due to the lack of good methods for its synthesis. Herein we report a short high yielding synthesis of a multiply C-13-labelled glycitein derivative, [2,3,4-C-13(3)]glycitein, which has been employed as an internal standard in LC-MS analysis. A key feature is a rapid and efficient synthesis of 2,4-dihydroxy-5-methoxy[1',2'-C-13(2)]acetophenone via acetylation of isovanillin with [C-13(2)]acetyl chloride followed by a Baeyer-Villiger reaction, selective hydrolysis and finally a BF3 catalysed Fries rearrangement. An aldol reaction using 4-benzyloxy-[carbonyl-C-13]benzaldehyde gave a chalcone and then thallium(III) mediated oxidative rearrangement, deprotection and cyclisation provided the [2,3,4-C-13(3)]glycitein. The overall yield for the 8 step reaction sequence, based on [C-13(2)]acetyl chloride, was 57%. (C) 2004 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)12211-12216
Number of pages6
JournalTetrahedron
Volume60
DOIs
Publication statusPublished - 20 Dec 2004

Keywords

  • isoflavones
  • glycitein
  • phytoestrogens
  • C-13-labelling
  • MASS-SPECTROMETRY
  • QUANTIFICATION
  • ISOFLAVONES
  • GLYCITEIN
  • DAIDZEIN
  • LIGNANS

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