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Total Synthesis of Picrinine

Abstract

Throughout history, organisms have ensured their survival by producing a wide variety of small molecule natural products. These entities commonly serve roles in cell function and signaling, and have also provided a defense system to combat infectious parasites. In the realm of synthetic chemistry, natural products serve as an architectural inspiration for the development of novel chemical transformations and molecular cascade processes. Ultimately, the synthesis of natural products that have biological importance holds promise toward the understanding of a plethora of biochemical pathways and the treatment of disease.

This dissertation describes synthetic efforts toward the alkaloid picrinine. This molecule is a member of the akuammiline alkaloid class, and it bears a complex molecular scaffold unaddressed by synthetic chemistry. Central to the synthetic approach is the use of the Fischer indolization reaction as a platform for rapidly building molecular complexity and constructing the salient furanoindoline core of picrinine. The earlier part of this dissertation describes a first-generation approach to the synthesis of picrinine, while the ensuing chapter concerns a second-generation route, which resulted in its total synthesis. This dissertation's final section concerns the development of a unified and enantioselective approach to the akuammiline alkaloid family, in addition to a formal enantioselective synthesis of both aspidophylline A and picrinine. In summary, the synthetic endeavors described emphasize the importance natural products hold for the development of novel synthetic strategies and transformations.

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