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Issue 0, 1987
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Synthesis of condensed tannins. Part 18. Stilbenes as potent nucleophiles in regio- and stereo-specific condensations: novel guibourtinidol-stilbenes from Guibourtia coleosperma

Abstract

(E)-3,3′,4,5′-Tetrahydroxy- and 3′,4,5′-trihydroxy-stilbenes function as strong nucleophiles in regio- and stereo-specific condensations with carbenium ions generated from 2,3-trans- and 2,3-cis-flavan-3,4,4′,7-tetraols (leucoguibourtinidins) to generate those [4,2]-‘dimeric’ and [4,2 : 4,6]-‘trimeric’ proguibourtinidin oligomers which occur in Guibourtia coleosperma. Problems of structural analysis associated with dynamic rotational isomerism and exceptional energy requirements for the coalescence of 1H n.m.r. resonances have been surmounted by synthesis. The requisite 3,3′,4,5′-tetrahydroxystilbene was prepared via a modified Reimann procedure.

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Article type: Paper
DOI: 10.1039/P19870001705
Citation: J. Chem. Soc., Perkin Trans. 1, 1987, 1705-1712
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    Synthesis of condensed tannins. Part 18. Stilbenes as potent nucleophiles in regio- and stereo-specific condensations: novel guibourtinidol-stilbenes from Guibourtia coleosperma

    J. P. Steynberg, D. Ferreira and D. G. Roux, J. Chem. Soc., Perkin Trans. 1, 1987, 1705
    DOI: 10.1039/P19870001705

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