Site-Selective Functionalization of a Versatile Lactam

A fundamental goal of organic synthesis is to identify methods where simple and easily accessible synthetic intermediates are converted into a diverse collection of products. The structural motifs, originating from a single intermediate, yield molecules with the potential for use in the chemical community. In this research, a highly functionalized, easily synthesized compound will be manipulated to produce motifs with the potential for use in pharmaceuticals. The compound of interest contains a lactam unit, which is commonly found in naturally biologically active compounds. Some lactam-containing compounds have also shown promise as antineoplastic agents. Another appealing aspect of the compound of interest is that it contains two stereocenters with known spatial arrangement. This allows for complete control over the stereochemistry of possible products. The importance of stereochemistry in pharmaceuticals is highlighted in the infamous case of thalidomide, a drug used worldwide to treat morning sickness in pregnant women in the 1950’s. The compound of interest has been used as the starting material in several chemical reactions and led to motifs showing potential biological activity against neglected tropical diseases