A multistep synthesis of quinolone antibiotic analogues was developed as a laboratory experiment for intermediate/advanced undergraduate students. Students can synthesize a range of "des"fluoroenoxacin analogues via a five-step sequence. The experiment includes a range of key practical laboratory techniques including thin-layer chromatography (TLC), liquid-liquid extraction, trituration, recrystallization, and the characterization of compounds by IR and NMR spectroscopy. The experiment provides an opportunity for students to carry out fundamental organic chemistry transformations from the curriculum such as the preparation of acyl chlorides, 1,4-conjugate addition-elimination, heterocycle synthesis, nucleophilic aromatic substitution, and ester hydrolysis. The five-step sequence does not require column chromatography and can be adapted to a range of laboratory settings.