Partial Synthesis of Novel Oxazolidinone Antibiotic Analogues
Date of Award
2017
Document Type
Thesis
Degree Name
Bachelors
Department
Natural Sciences
First Advisor
Scudder, Paul
Area of Concentration
Chemistry
Abstract
Worldwide, 700,000 people die of infections from resistant bacteria each year. The emergence of resistance can happen as quickly as overnight with a single point mutation, arming bacteria with resistance to entire classes of drugs. With few antibiotic breakthroughs in recent decades, scientists have been left scrambling to catch up. This thesis details the attempted synthesis of oxazolidinone analogues with the goal of increased efficacy in Gram-negative and other resistant bacteria. The objective was to vary the C-position of oxazolidinones with different amino acid-substituted heteroaromatics. Three routes were explored. First, a scheme for the parallel synthesis of multiple analogues using Suzuki coupling was investigated only to find that both the borylation of a model system and model Suzuki couplings failed. Secondly, an oxadiazole analogue was pursued. However, the furthest progress made with this route was the formation of an ester intermediate to the oxadiazole on a model system. Lastly, a one-pot synthesis of a triazole analogue was attempted. With the most hopeful results of the three routes, a model triazole was successfully synthesized, but the actual analogue failed to form. However, only one reaction must be executed to obtain a testable triazole analogue.
Recommended Citation
Cheng, Ana, "Partial Synthesis of Novel Oxazolidinone Antibiotic Analogues" (2017). Theses & ETDs. 5320.
https://digitalcommons.ncf.edu/theses_etds/5320