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. 2005 Aug 8;61(32):7703-7711.
doi: 10.1016/j.tet.2005.05.086.

Asymmetric total synthesis of B-ring modified (-)-epicatechin gallate analogues and their modulation of beta-lactam resistance in Staphylococcus aureus

James C Anderson  1 , Catherine Headley, Paul D Stapleton, Peter W Taylor
Affiliations

Asymmetric total synthesis of B-ring modified (-)-epicatechin gallate analogues and their modulation of beta-lactam resistance in Staphylococcus aureus

James C Anderson et al. Tetrahedron. .

Abstract

Two enantiomerically pure B-ring modified analogues of (-)-epicatechin gallate were synthesised and their modulation of beta-lactam resistance using three strains of methicillin resistant Staphylococcus aureus (BB 568, EMRSA-15 and EMRSA-16) evaluated. Sub-inhibitory concentrations (12.5 and 25 mg/L) of the two analogues fully sensitised each of the three MRSA strains to oxacillin, reducing the MIC to less than 0.5 mg/L, identical to levels achieved with ECg. Lower concentrations demonstrated that the position and degree of hydroxylation of the B-ring is important for activity.

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