Date of Award
Bachelor of Science (BS)
Dr. Anne Reeve
Aspernigrin A (6-benzyl-4-oxo-1,4-dihydropyridine-3-carboxamide)is a natural product isolated from the fungus Aspergillus nigerfound in the Mediterranean sea sponge, Axinelladamicornis. This secondary metabolite has proven to becytotoxic to certain 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 new synthetic pathway being tested utilizes ethyl acetoacetateto create an enaminone capable of being directly converted to the pyridinone required for aspernigrin A. Through reaction in a DMF-Me2SO4adduct, ethyl acetoacetatewas successfully reacted to give the enaminone product, ethyl-2-[(dimethylamino)methylene]-3-oxobutanoate, at an averageyieldof 79%. Subsequent reaction of the enaminone with n-BuLi, LiHMDS, and phenylacetyl chloride showed promise for the production of the pyridinone ethyl ester,3-carbethoxy-6-phenyl-4(1H)-pyridinone. Continued optimization of this reaction scheme will allowgreaterproduction of the enaminone and subsequent reaction to form the pyridinone ethyl ester that could eventually yield aspernigrin A.
Marburger, Brady and Reeve, Anne, "A Novel Synthetic Pathway for Aspernigrin A" (2016). Honors Projects and Presentations: Undergraduate. 63.