Date of Award

2010

Document Type

Thesis

Degree Name

Bachelor of Arts (BA)

Department

Health, Nutrition and Exercise Science

First Advisor

Dr. Anne Reeve

Abstract

Aspernigrin A (6-benzyl-4-oxo-1,4-dihydropyridine-3-carboxamide) (1) is a natural product isolated from the fungus Aspergillus niger found in a Mediterranean sea sponge, Axinella damicornis. This secondary metabolite has proved cytotoxic to colon cancer cell lines. The synthesis of Aspernigrin A is required to obtain enough material to study its bioactivity and potentially optimize it for clinical drug use. The best proposed plan is a multistep process requiring the preliminary production of a specific starting compound, 4-hydroxy-6-phenylmethyl-2-pyrone (6). This pyrone is not obtainable commercially and must first be synthesized. After attempting several different reactions, the first step of the pyrone synthesis was achieved by the bromination of dehydroacetic acid using N-bromosuccinimide in an organic solvent of carbon tetrachloride. The reaction was irradiated under a 160W UV lamp and a 56% product yield was verified using 1H NMR spectroscopy. The reaction product (14) was subsequently treated to various separation methods in attempt to isolate it from the starting material. Success of this isolation would allow progression to the next phase of the synthetic reaction scheme of Aspernigrin A (1).

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