Mentor: Professor William Malachowski
The ability to synthesize complex analogs of natural products with specific stereochemistry is important in the development of safe bioactive molecules for use as therapeutic treatments. One specific challenge is the enantioselective synthesis of stereogenic quaternary carbon centers. These quaternary carbon centers are present in bioactive molecules such as cortisone, morphine, and vitamin D3. With the successful synthesis of (+)-mesembrine through a Birch reduction-allylation reaction followed by hydrolysis and subsequently Cope rearrangement, we hope to be able synthesize (+)-lycoramine. Lycoramine is similar to galanthamine; the structures differ by only the presence of absence of one double bond. Galanthamine has been recently approved as a drug for the treatment of Alzheimer’s disease and lycoramine has been found to be nearly as potent a drug.