Abstract
Depsidones are a class of natural products that exhibit potent antibacterial activity (MIC = 0.0825-8 μg/mL) against vancomycin and methicillin resistant staphylococcus aureus. In order to increase the antibiotic potency of the depsidone family of natural products, modifications in size and connectivity are being explored. Although a synthesis for the core 6,7,6-fused tricyclic structure of depsidone exists, the yields of the final products are low. In an effort to optimize the yields, a new synthesis has been derived which involves Chan-Lam copper catalyzed coupling of diversified boronic acids and a substituted diol, amine hydroxyl, and thiol hydroxyl benzene rings followed by deprotection and esterification steps to close the central ring. Following this same synthesis, the core structure of depsidone was modified to change the ester linkage to both an amide and a thioester. These changes provided insight into the effect the electronic interactions have on antibiotic activity. All analogs synthesized have been evaluated in an antibacterial assay against Gram-positive and Gram-negative bacteria in order to build a structure activity relationship profile around depsidone core modifications.
How to Cite
Nutt, C., (2018) “Synthesis and Evaluation of Modifications to the Central Ring of Depsidone Natural Products”, Capstone, The UNC Asheville Journal of Undergraduate Scholarship 31(1).
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