Date of Award
Bachelor of Science (BS)
Chemistry and Biochemistry
Dr. Anne Reeve
Many natural products have been found to be beneficial in medicinal applications. Aspernigrin A, a secondary metabolite from a strain of Aspergillus niger, was isolated from the Mediterranean sea sponge Axinella damicornis. Preliminary assays of aspernigrin A showed moderate cytotoxicity to the colon cancer cell line SW1116. Due to its limited availability from the producer organisms and relatively simple structure, it was hypothesized that the compound and structural analogs could be synthesized. Several synthetic strategies have been explored in the past years. The current pathway begins with installing a benzyl ether protecting group on the commercially available 4-hydroxy-6-methyl-2-pyrone followed by SeO2 oxidation to the 6-oxo derivative in greater than 50% yield over two steps. The subsequent reactions, reduction of the aldehyde to the corresponding alcohol, conversion of the alcohol to a suitable leaving group, and a Suzuki coupling reaction with phenylboronic acid, are well established in organic chemistry and will be pursued to synthesize aspernigrin A.
Lemen, Daniel J.; Cross, Zebulun; McDermond, Duncan; and Reeve, Anne, "A Novel Synthetic Pathway for Aspernigrin A" (2018). Honors Projects and Presentations: Undergraduate. 50.