Photochemical deoxygenation of an α-ketol: the dihydroflavonol–flavanone conversion

Authors:
  • JWJan H. van der Westhuizen
    Jan H. van der Westhuizen
  • DFDaneel Ferreira
    Daneel Ferreira
  • DRDavid G. Roux
    David G. Roux
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Abstract
Irradiation of optically pure 2,3-trans-3-hydroxyflavanones in anhydrous ethyl acetate leads directly to free phenolic flavanone analogues with complete retention of configuration at C(2). Similarly their methyl ethers give the corresponding flavanones and flavones. The reaction represents the photochemical equivalent of a reduction under Clemmensen conditions.