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New Organocatalytic Malononitrile Michael Addition Methodology for the Enantioselective Synthesis of Calyciphylline K (CATSYNCAL)
Start date: Mar 4, 2014, End date: Mar 3, 2016 PROJECT  FINISHED 

Calyciphylline K is a Daphnezomine L-type natural product with promising anticancer activity. We propose to complete the total synthesis of Calyciphylline K and several closely-related Daphnezomine L alkaloids by developing a novel asymmetric organocatalytic Malononitrile Michael Addition methodology to facilitate their preparation in a short sequence of around 12 synthetic steps. The anticancer activity of Calyciphylline K and other analogues prepared during this study will then be evaluated using Alamar Blue cell viability assays, followed by further study in collaboration with the Structural Genomics Consortium (SGC), where high-throughput kinase screening assays are available to further understand their pharmacological mode of action. This project will provide significant advances in the field of organocatalysis (new methodology for asymmetric synthesis), natural product synthesis (first preparation of the Daphnezomine L alkaloids) and anticancer medicinal chemistry and pharmacology (exploration and study of biological activities).
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