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"For this project, we attempted a new synthesis of Chloramphenicol, An antibiotic used that inhibits the protein synthesis in bacteria. This involves a series of reactions, some of which were to create materials which were unavailable to us, and some of which were essential to the production of the compound. First, we carried out an acylation reaction between Dichloroacetyl Chloride and Aminoacetaldehyde dimethyl acetal with triethylamine to act as a base and ethyl acetate as a solvent. Then, that product underwent a hydrolysis using THF and 2M HCl to convert the acetal to an aldehyde which went in about 75% yield. L-proline was then used to catalyze a reaction in conjunction with DMSO to add 1 equivalent of P-nitrobenzaldehyde to the aldehyde product, which should result in one hydroxyl group facing forward and another one facing backward. L-proline acts to add the hydroxyl groups in a stereochemically-specific way, which should be the D-threo conformation. That reaction was based on a publishing in the Journal of the American Chemical Society by Carlos F. Barbas III, et al. The next reaction involved reduction by Sodium Borohydride to reduce the aldehyde to the corresponding alcohol."
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