Crystal structure and absolute configuration of (–)-3-O-acetyl-6-bromo-3′,4′,5,7-tetra-O-methylepicatechin, a reference compound for the aromatic bonding positions of 2,3-cis-procyanidins
- 1 January 1986
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 2,p. 301-303
- https://doi.org/10.1039/p29860000301
Abstract
Determination of the structure of (–)-(2R,3R)-3-O-acetyl-6-bromo-3′,4′,5,7-tetra-O-methylepicatechin in the crystalline state confirmed the position of bromination and hence that of its 8-bromo isomer; both are key reference compounds for assessing the aromatic bonding positions in 2,3-cis-procyanidins. The half-chair conformation of the heterocyclic ring is shown to be in close agreement with the published structure of (–)-epicatechin. Determination of the absolute configuration of the derivative, in accord with earlier chemical evidence, is shown to hinge on detailed refinement of an extended data set.Keywords
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