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Wednesday, April 26 • 1:20pm - 1:40pm
Optimization Of Synthesis And Antibiotic Evaluation Of Heterocyclic Depsidone Analogs

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Depsidone natural products are potent inhibitors of Gram-positive bacteria, with MIC values ranging from 0.1–8.0 μg/mL. By synthesising various heterocyclic depsidone analogs and testing them on antibacterial assays, the antibiotic activity against Staphylococcus aureus will be observed as well as its correlation with the electronic profile of the analog. Synthesis and optimization of pyridine, furan, and thiophene depsidone analogs has been accomplished through an optimized 4-step synthetic sequence beginning from the corresponding 2-carboxyphenylboronic acid heterocycles. After the methyl protection of the heterocycle is achieved, the central 7 membered ring of each depsidone analog is produced by first coupling to catechol through a Cu(OAc)2 catalyzed reaction (12-25% yield), deprotection of the methyl ester (57% yield), and closing the ring through an intramolecular esterification. Each analog will be tested in an antibacterial bioassay against Staphylococcus aureus to reveal how the changes in the electronic profile affect antibiotic activity.


Wednesday April 26, 2017 1:20pm - 1:40pm PDT
014 Zeis Hall