Novel reaction products from the hypervalent iodine oxidation of hydroxylated stilbenes and isoflavones

Cedric J. Lion, David A. Vasselin, Carl H. Schwalbe, Charles S. Matthews, Malcolm F.G. Stevens, Andrew D. Westwell*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


Novel reaction pathways for the hypervalent iodine-mediated oxidation of bioactive phenols containing extended conjugated π-systems are described. Oxidation of 4-hydroxystilbenes in methanol using a hypervalent iodine-based oxidant led to the formal 1,2-addition of methoxy groups across the central stilbene double bond. Treatment of the structurally related 4-hydroxyisoflavone with di(trifluoroacetoxy)iodobenzene leads to the surprising formation of 2,4′-dihydroxybenzil. Potential mechanisms for these new reaction pathways are discussed, and the X-ray crystal structure of 2,4′-dihydroxybenzil is presented. In contrast, oxidation of the corresponding 3-hydroxystilbenes and 3-hydroxyisoflavone led to conventional dienone oxidation products. The antitumour implications of these oxidation processes are briefly highlighted; the novel 4-substituted phenolic oxidation products were found to be inactive in terms of in vitro antitumour cellular activity, whereas the 3-substituted phenol products gave novel agents with potent and enhanced antitumour activity in the HCT 116 cancer cell line. © The Royal Society of Chemistry 2005.

Original languageEnglish
Pages (from-to)3996-4001
Number of pages6
JournalOrganic and Biomolecular Chemistry
Issue number21
Early online date4 Oct 2005
Publication statusPublished - Nov 2005


  • hypervalent iodine-mediated oxidation
  • bioactive phenols
  • methoxy groups
  • 2,4'-dihydroxybenzil
  • HCT 116 cancer cell line


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