(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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Journal of the Chemical Society, Perkin Transactions 1
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