105072-75-1Relevant academic research and scientific papers
Synthesis of Condensed Tannins. Part 16. Stereochemical Differentiation of the First 'Angular' (2S,3R)-Profisetinidin Tetraflavanoids from Rhus lancea (Karree) and the Varying Dynamic Behaviour of their Derivatives
Young, Desmond A.,Kolodziej, Herbert,Ferreira, Daneel,Roux, David G.
, p. 2537 - 2544 (2007/10/02)
Four novel 'angular' diastereoisomeric profisetinidin tetraflavanoids, shown to be constituted of (2S,3R)-(+)-fisetinidol and -bi- substituents at C-6 and C-8 on the enantiomeric (2R,3S)-(+)-catechin moiety, occur in the heartwood of Rhus lancea.Structural and stereochemical differentiation was provided by synthesis of their tridecamethyl ether tetra-acetates.Our earlier allocation of a 'linear' arrangement of flavanyl units for one of the isomers is accordingly revised to an 'angular' assignment comprising -bi- and -2,3-trans-3,4-trans-(+)-fisetinidol substituents on (+)-catechin.Its derivative exhibits 'static' and the remainder varying degrees of 'dynamic' behaviour in solution, relative configurations determining their relative rotational stabilities.The first 'branched' profisetinidin pentaflavanoid homologue resulted as synthetic byproduct.
