Development of Fragment Coupling Methodologies and the Application to Natural Product Synthesis

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Small molecules such as indanes, chromanes, tetralins and their derivatives play a significant role in drug discovery due to their potent biological activity. This research herein presents a facile Brønsted acid-catalyzed allylsilane annulation methodology to generate fused ring systems such as indanes. The reaction goes through a homoallylic intermediate which then readily cyclizes to form the desired product. Different types of fused ring systems such as chromanes and lignan natural products can be accessed in a similar fashion using differently substituted allylsilanes and benzyl alcohol species. Structural complexity was rapidly built from simple precursors. ', 'The second part of the research focuses on developing a “traceless†variant of the Petasis Borono-Mannich reaction. A one-pot synthesis of allylic alcohols by the sulfonylhydrazide-mediated coupling of aldehydes with alkenyl trifluoroborates was achieved. The process involves in situ generation of a hydrazone species and subsequent loss of N2. Further development of the methodology is still underway.

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  • 10/14/2019
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