Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 19, Issue 21, Pages 4743-4751Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1ob00717c
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- Ministry for Science & Culture of the German State of Lower Saxony (MWK) [2178904-63-5/19]
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The synthetic berkeleylactone A was shown to inhibit the formation of Staphylococcus aureus biofilms and exhibit significant dispersive effects on preformed biofilms of Candida albicans.
The fungal macrolide berkeleylactone A was synthesised in 13 steps and 24% yield using (R)-propylene oxide and an asymmetric Noyori hydrogenation of a beta-ketoester to install the stereogenic centres. A domino addition-Wittig olefination of a 13-hydroxytetradecanal intermediate with the cumulated ylide Ph3PCCO closed the macrocyle by establishing the alpha,beta-unsaturated ester group, necessary for the attachment of the sidechain thiol via a thia-Michael reaction. The synthetic berkeleylactone A inhibited the formation of Staphylococcus aureus biofilms and showed significant dispersive effects on preformed biofilms of Candida albicans by at least 45% relative to untreated controls at concentrations as low as 1.3 mu g mL(-1).
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