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Synthesis of the fungal macrolide berkeleylactone A and its inhibition of microbial biofilm formation.
Schriefer, Manuel G Schrey, Hedda Zeng, Haoxuan Schobert, Rainer
Schriefer, Manuel G
Schrey, Hedda
Zeng, Haoxuan
Schobert, Rainer
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2021-05-03
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Abstract
The fungal macrolide berkeleylactone A was synthesised in 13 steps and 24% yield using (R)-propylene oxide and an asymmetric Noyori hydrogenation of a β-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 α,β-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 μg mL-1.
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Org Biomol Chem. 2021 Jun 2;19(21):4743-4751. doi: 10.1039/d1ob00717c.
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en
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1477-0539
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Attribution 4.0 International