Synthesis of condensed tannins. Part 13. The first 2,3-trans-3,4-cis-procyanidins: sequence of units in a ‘trimer’ of mixed stereochemistry
- 1 January 1985
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 4,p. 669-676
- https://doi.org/10.1039/p19850000669
Abstract
The condensation of (+)-leucocyanidin with (–)-epicatechin initiates a succession of substitutions leading mainly to the introduction of [4,8]-2,3-trans-3,4-trans-procyanidin units, but also to the incoporation of ‘terminal’ moieties which possess the hitherto unique 3,4-cis-procyanidin configuration. The bonding patterns in the products, and also the sequence of units in one of the ‘trimers’ of mixed stereochemistry, are resolved by 1H n.m.r. spectroscopy through selective use of solvents at elevated temperatures.This publication has 8 references indexed in Scilit:
- Synthesis of isoflavanoid oligomers using a pterocarpan as inceptive electrophileJournal of the Chemical Society, Perkin Transactions 1, 1984
- Synthesis of condensed tannins. Part 11. Intramolecular enantiomerism of the constituent units of tannins from the anacardiaceae: stoicheiometric control in direct synthesis: derivation of 1H nuclear magnetic resonance parameters applicable to higher oligomersJournal of the Chemical Society, Perkin Transactions 1, 1983
- Synthesis of condensed tannins. Part 9. The condensation sequence of leucocyanidin with (+)-catechin and with the resultant procyanidinsJournal of the Chemical Society, Perkin Transactions 1, 1983
- Synthesis of condensed tannis. Part 8. The first ‘Branched’[4,6 : 4,8 : 4,6]-tetraflavanoid. Coupling sequence and absolute configurationJournal of the Chemical Society, Perkin Transactions 1, 1983
- Synthesis of condensed tannins. Part 7. Angular [4,6 : 4,8]-prorobinetinidin triflavanoids from black wattle (‘Mimosa’) bark extractJournal of the Chemical Society, Perkin Transactions 1, 1983
- Synthesis of condensed tannins. Part 6. The sequence of units, coupling positions and absolute configuration of the first linear [4,6 : 4,6]-triflavanoid with terminal 3,4-diol functionJournal of the Chemical Society, Perkin Transactions 1, 1982
- Plant proanthocyanidins. Part 6. Chiroptical studies. Part 95. Circular dichroism of procyanidinsJournal of the Chemical Society, Perkin Transactions 1, 1979
- Condensed tannins. Circular dichroism method of assessing the absolute configuration at C-4 of 4-arylflavan-3-ols, and stereochemistry of their formation from flavan-3,4-diolsJournal of the Chemical Society, Chemical Communications, 1978