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Synthesis 1992; 1992(5): 436-438
DOI: 10.1055/s-1992-26127
short paper
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Dimethyldioxirane Epoxidation of Aurones and Isoflavones

Waldemar Adam* , Lazaros Hadjiarapoglou, Albert Levai
  • *Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-8700 Würzburg, Germany
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Publication Date:
17 September 2002 (online)

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The synthesis of the corresponding epoxides 2 and 4 by epoxidation of aurones (2-benzylidenebenzofuran-3(2H)-ones, 1) and isoflavones (3-aryl-4H-1-benzopyran-4-ones,3) with dimethyldioxirane at subambient temperatures is reported. These acid- and base-sensitive epoxides, which have been previously difficult to prepare, were isolated in excellent yields and were completely characterized by spectral and microanalytical data. The now readily available aurone and/or isoflavone oxides may serve as convenient precursors to flavonoid-type natural products.

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