Date of Submission
Academic Programs and Concentrations
Chemistry; Environmental and Urban Studies
Project Advisor 1
The bis-indole alkaloid violacein is a prospective antimicrobial therapeutic primarily isolated as a secondary metabolite from bacterial cell cultures. An efficient, environmentally benign methodology for synthesizing the natural product and a series of analogs has been developed. The violacein scaffold is produced in the thermally driven, sequential condensation of a γ-ketoester with ammonium acetate and isatin in polyethylene glycol. This three-component, microwave-mediated cyclization has been optimized to produce the 3,5-disubstituted 2H-pyrrol-2-one core of violacein in good yield, enabling the convenient preparation of analogs. These analogs may include protecting groups that can be cleaved to obtain violacein’s hydroxyl substituent at the 5-potition of the indole moiety, and unprotected nitrogen on the isatin component. Relevant spectral data has been collected for the intensely purple compounds, which will be entered into a library for biological screening.
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Norman, Matthew W., "Synthesis and Characterization of the Antimicrobial Bisindole Alkaloid Violacein and Analogs" (2014). Senior Projects Spring 2014. Paper 105.