Because of heavy antibiotic usage, bacteria have developed resistance to antimicrobial agents. Due to the heavy resistance bacteria are showing, novel antibacterial agents must be synthesized. One novel antibacterial agent that has been developed is Oxazolidinone antibacterial agents. This class of antibiotics utilizes a novel mechanism that inhibits the bacteria’s ability to synthesize protein. This research’s goal was to synthesize a novel Oxazolidinone with a benzodioxin ring system containing an alcohol functional group. Because of the alcohol’s acidic proton, the synthesis began using a protected aldehyde. The aldehyde was protected with an acetal group due to its low reactivity with the reagents used. At the end of the synthesis, the aldehyde was deprotected and reduced to an alcohol. This added group allows the molecule to hydrogen bond, becoming more soluble and reducing the toxic effects seen in current oxazolidinone antibiotics. Synthesis of this molecule includes 11 steps. After synthesis, the compound will be analyzed at Johns Hopkins University to determine how active the molecule is towards resistant strains of bacteria.

Synthesis of a novel oxazolidinone antibacterial agent containing an alcohol functional group

255th National Meeting (2018)

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