Date of Award

2014

First Advisor

David Myers

Second Advisor

Erin McMullin

Abstract

Marine sponges have been shown to contain butenolide compounds that have antibiotic and antifungal activity, but they only make these compounds on a milligram scale (Hamada, 2005). With bacterial and fungal resistance increasing in modern society, a means for making new antibiotic and antifungal agents on a large-scale becomes necessary. This thesis discusses a step-by-step synthesis of target butenolide compounds, similar to those found in marine sponges, which have potential antibiotic activity (Jakubowski et al., 1982). Over the course of ten months, synthesis of target butenolide compounds was almost completed, and a number of alkynoic acids, and one butenolide, were tested for antibiotic and antifungal activity using the Kirby-Bauer disc assay (Hudzicki, 2013). All compounds tested were found to have activity against S. aureus. While the synthetic scheme was not completely finished, carbon backbones were built with varying unsaturations and methylations, which could allow for the large-scale production of a potentially endless variety of alkynoic acids and butenolides with possible biological activity. This could open up an entire new area of antibiotic and antifungal compounds for the future of Western medicine.

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