69127-09-9Relevant articles and documents
Synthesis of Condensed Tannins. Part 7. Angular -Prorobinetinidin Triflavanoids from Black Wattle ('Mimosa') Bark Extract
Viviers, Phillip M.,Botha, Jacobus J.,Ferreira, Daneel,Roux, David G.,Saayman, Henry M.
, p. 17 - 22 (1983)
The triflavanoid fraction from the bark extract of the black wattle (Acacia mearnsii) comprises five angular prorobinetinidins with their constituent robinetinidol units -linked to both (+)-catechin and (+)-gallocatechin.Synthetic proof of structure is provided for three bi--(+)-catechin diastereoisomers.The complete dominance of prorobinetinidins in the higher oligomeric fractions correlates with the faster condensation rate of the parent (+)-leucorobinetinidin with the nucleophilic substrates compared with competing (+)-leucofisetinidin.
Synthesis of Condensed Tannins. Part 4. A Direct Biomimetic Approach to - and -Biflavanoids
Botha, Jacobus, J.,Ferreira, Daneel,Roux, David G.
, p. 1235 - 1245 (2007/10/02)
The generation of flavanyl-4-carbo-cations from flavan-3,4-diols and their condensation with nucleophilic flavan-3-ols to form - and -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.