Date of Award

2014

Document Type

Thesis

First Advisor

Dr. Anne Reeve

Abstract

Aspernigrin A (2) is a secondary metabolite obtained from the fungus Aspergillus niger found on the Mediterranean sea sponge Axinella damicornus. This compound has been seen to exhibit inhibitory properties on the growth of the human colon cancer cell line SW1116, as well as xanthine oxidase, making it a potential drug candidate. Several synthetic schemes have been proposed for the synthesis of aspernigrin A involving the bromination of a methyl group to activate the position for a cross-coupling reaction to join a phenyl group to the more substituted ring of aspernigrin A. One such scheme involves the bromination of 6-methyl-1,4-dihydro-4- oxopyridine-3-carboxylic acid (6), which is synthesized in two steps from 4-hydroxy-6-methyl2-pyrone (3). These two steps, being the reaction of (3) to form 3-(dimethylaminomethylene)-4- oxo-6-methyl-2-pyrone (5) and the reaction of (5) to form 6-methyl-1,4-dihydro-4-oxopyridine3-carboxylic acid (6), have been successfully completed. The third step, bromination of the 6- methyl position of (6), has been attempted but yet to be accomplished.

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