Regio- and stereoselective oxidation of flavan-3-ol- 4-arylflavan-3-ol- and biflavanoid derivatives with 2,3-dichloro-56-dicyano-1,4-benzoquinone (DDQ)

  • Steenkamp J
  • Mouton C
  • Ferreira D
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Abstract

The phenolic methyl ethers of flavan-3-ols, 4/gb-arylflavan-3-ols, and (-)-fisetinidol-(4β,8)-(+)-catechin biflavanoids are susceptible to regio- and stereoselective methoxylation at C-4 in moderate yields with DDQ in CHCl3-MeOH solution. The observed asymmetric induction with exclusive formation of 2,4-trans products is compatible with the intermediacy of a diastereogenic donor-acceptor interaction, DDQ acting as the acceptor and oxidant. The 4-funtionalized analogues are of both synthetic and degradative significance in condensed tannin chemistry. © 1991.

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Authors

  • Jacobus A. Steenkamp

  • C. Hendrik L. Mouton

  • Daneel Ferreira

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