title: Improved synthesis of structural analogues of (-)-epicatechin gallate for modulation of staphylococcal β-lactam resistance.
abstract: The high-yielding synthesis of enantiomerically pure epicatechin gallate analogues where the A and/or B-ring hydroxylation is reduced or altered has been achieved by optimising routes to the catechin stereochemistry. The B-ring analogues were synthesised by using an electrophilic ring closure onto an enantiomerically enriched epoxide as a key step. The A and B-ring hydroxyl-deleted analogues were synthesised through a Mitsunobu cyclisation. For the B-ring analogues, theanti- (catechin) stereochemistry was converted to thesyn- (epicatechin) stereochemistry by a known oxidation/reduction protocol. Absolute stereochemistry was derived from either a Sharpless epoxidation or asymmetric dihydroxylation.
authors.affiliation: Department of Chemistry, University College London, 20 Gordon Street, London WC1H 0AJ, UK.
authors.forename: James C
authors.initials: JC
authors.lastname: Anderson
authors.affiliation: Department of Chemistry, University College London, 20 Gordon Street, London WC1H 0AJ, UK.
authors.forename: Helen
authors.initials: H
authors.lastname: Grounds
authors.affiliation: Department of Chemistry, University College London, 20 Gordon Street, London WC1H 0AJ, UK.
authors.forename: Suzanna
authors.initials: S
authors.lastname: Reeves
authors.affiliation: School of Pharmacy, University College London, 29-39 Brunswick Square, London WC1, 1AX, UK.
authors.forename: Peter W
authors.initials: PW
authors.lastname: Taylor
keywords: (−)-Epicatechin gallate analogues; Asymmetric synthesis; Cyclisation; MRSA; Mitsunobu