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Michael Calter




This thesis outlines the development and optimization of the synthesis of an analog to a common nucleophile used in the Interrupted Fesit-Bénary reaction. This nucleophile is proposed to be more stable under acidic conditions, while still allowing further functionalization after the IFB reaction. The nucleophile was then utilized in an attempted total synthesis of the natural product hydroxybrazilin, which has a myriad of interesting therapeutic activities and industrial applications. The new analog proved to be lower yielding comparatively, and unfortunately did not provide the extra stability under acidic conditions that was desired. This did provide mechanistic insight, and the shorter sidechain was easier to work with in some of the later stages of the synthesis. We are also able to use this information to propose future routes and strategies that may lead to the total synthesis of hydroxybrazilin from the same starting materials.

The synthesis of the electrophile was also optimized, along with some alterations to the synthetic steps following the IFB reaction due to the differences between our new nucleophile and the old one.



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