For many years the diverse molecular architectures of natural products have been a major source of inspiration for both novel reaction development and therapeutic lead molecules. The marine environment has become one of the most prolific sources of chemical and biological diversity. One such example is the recently isolated apoptosis-inducing pentacyclic guanidinium alkaloid, monanchocidin A. The intricacy and novelty observed in the structure of the pentacyclic guanidinium alkaloids such as the monanchocidin family, coupled with the wide range of biological activities exhibited by these molecules, have attracted significant attention from the scientific community. We are developing an approach to the pentacyclic guanidinium core of the monanchocidins and related natural products that overcome the stereochemical challenges associated with the previous syntheses of this class of natural products and utilize these scaffolds as chemical probes in biological assays. Our recent efforts in this area will be presented.

Total synthesis of the pentacyclic guanidinium core of apoptosis-inducing marine natural products

251st National Meeting (2016)

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