Issue 5, 1988

Oligomeric isoflavonoids. Part 2. Structure and synthesis of xanthocercin A and B, the first isoflavono-lignoids

Abstract

The structures of xanthocercin A and B, the first Isoflavono-lignoids, have been established as 2,3-trans-3-(4-hydroxy-3,5-dimethoxyphenyl)-8-(3-hydroxy-4-methoxyphenyl)-2-hydroxymethyl-2,3-dihydro-7H-1,4-dioxino[2,3-h]chromen-7-one (1) and 2,3-trans-8-(3-hydroxy-4-methoxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-2,3-dihydro-7H-1,4-dioxino[2,3-h]chromen-7-one (3) respectively by spectroscopic methods. These structures have been confirmed by synthesis via phenol oxidative coupling of the appropriate 7,8-dihydroxyisoflavone and respectively sinapyl and coniferyl alcohol. The natural occurrence of xanthocercin A and B as single regioisomers and their regiospecific formation during synthesis presumably originate from marked differences in susceptibility to oxidation of the hydroxy functions in their ‘catechol precursors’.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1988, 1237-1241

Oligomeric isoflavonoids. Part 2. Structure and synthesis of xanthocercin A and B, the first isoflavono-lignoids

S. C. Bezuidenhout, B. C. B. Bezuidenhoudt, E. V. Brandt and D. Ferreira, J. Chem. Soc., Perkin Trans. 1, 1988, 1237 DOI: 10.1039/P19880001237

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