Journal of the Chemical Society. Perkin transactions I p. 1235 - 1245 (1981)
Update date:2022-08-04
Topics:
Botha, Jacobus, J.
Ferreira, Daneel
Roux, David G.
The generation of flavanyl-4-carbo-cations from flavan-3,4-diols and their condensation with nucleophilic flavan-3-ols to form <4,6>- and <4,8>-biflavanoids at ambient temperatures and mildly acidic aqueous conditions apparently simulates the initial step in condensed tannin formation in a number of natural sources.The stereospecificity (or stereoselectivity) of the reaction is conditioned mainly by the 2,3-cis or 2,3-trans stereochemistry of the parent flavan-3,4-diol, but also by the nuclephilicity of the flavan-3-ol, and its regiospecific (or regioselective) course by steric factors arising from variation in substitution of the receptive A-ring of the flavan-3-ol.
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