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Org Biomol Chem ; 14(35): 8253-60, 2016 Sep 21.
Article in English | MEDLINE | ID: mdl-27519121

ABSTRACT

A new antibiotic natural product, ravynic acid, has been isolated from a Penicillium sp. of fungus, collected from Ravensbourne National Park. The 3-acylpolyenyne tetramic acid structure was definitively elucidated via synthesis. Highlights of the synthetic method include the heat induced formation of the 3-acylphosphorane tetramic acid and a selective Wittig cross-coupling to efficiently prepare the natural compounds carbon skeleton. The natural compound was shown to inhibit the growth of Staphylococcus aureus down to concentrations of 2.5 µg mL(-1).


Subject(s)
Anti-Bacterial Agents/chemical synthesis , Penicillium/chemistry , Pyrrolidinones/chemical synthesis , Alkynes/chemistry , Anti-Bacterial Agents/isolation & purification , Anti-Bacterial Agents/pharmacology , Humans , Phosphoranes/chemical synthesis , Propanols/chemistry , Pyrrolidinones/chemistry , Pyrrolidinones/isolation & purification , Pyrrolidinones/pharmacology , Staphylococcus aureus/drug effects
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