A convenient and general synthesis of trans-3-hydroxyflavanones from chalcones by dimethyldioxirane epoxidation and subsequent base-catalyzed cyclization

Tamás Patonay, Gábor Tóth, Waldemar Adam

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Abstract

2′-Hydroxychalcone epoxides were found to give trans- 3-hydroxyflava-none and 2-(α-hydroxybenzyl)-3-coumaranone under basic conditions. Epoxidation of 2′-hydroxychalcones with dimethyldioxirane followed by treatment of tetra-butylammonium hydroxide provides a convenient and general method for the synthesis of trans-3-hydroxyflavanones.

Original languageEnglish
Pages (from-to)5055-5058
Number of pages4
JournalTetrahedron Letters
Volume34
Issue number32
DOIs
Publication statusPublished - Aug 6 1993

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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