UNC WilmingtonResearch Assistant
May. 2014 - May. 2015University of North Carolina Wilmington Department of Chemistry and BiochemistryTRAPPING CYCLOPENTADIENOL: APPLICATIONS TO THE SYNTHESIS OF KUCHINOENAMINE ANALOGS Kuchinoenamine is an alkaloid isolated from a marine sponge of the genus Hexadella in 2005 and was determined to have moderate antibacterial activity against Aeromonas hydrophila, a bacterium which infects fish, amphibians, and humans. Due to kuchinoenamine's limited availability in sponges and modest antibacterial activity, it is necessary to find ways to synthetically produce this compound and analogs if it is to be further evaluated and optimized as a medicinal compound. Cyclopentadienol forms from the decomposition of ferrocenium hexafluorophosphate and dimerizes to produce the crystalline tricyclic core of kuchinoenamine. This project evaluated the feasibility of trapping the cyclopentadienol with added external dienophiles. Maleic anhydride, N-benzylmaleimide, and 1,4-naphthoquinone, among others, were shown to be competent dienophiles, producing novel analogs of the kuchinoenamine tricyclic core in good-to-excellent yields after optimization. These analogs have been transferred to microbiologists at UNCW to be screened for antibiotic activity. The product formed using 1,4-naphthoquinone was determined to have antibacterial activity against Staphylococcus epidermidis, normal flora which can lead to nosocomial infections. Further reactions will be performed to systematically alter the structure of this compound in order to determine how changes in structure impact its antibacterial activity.