PhD defenses.

Total Synthesis of (2R)-hydroxynorneomajucin and Development of Strategies for the Assignment of Absolute Stereochemistry

Abstract:

Illicium sesquiterpenes have garnered significant interest from synthetic chemists owing to their highly oxidized structures and potent biological activity. In this talk, I will discuss my efforts toward the total synthesis of (2R)-hydroxynorneomajucin, a neuroprotective norsesquiterpene isolated from Illicium Jiadifengpi. I will discuss challenges faced and the evolution of our synthetic strategy, which has culminated in the first total synthesis of (2R)-hydroxynorneomajucin.

Developing New Rh–H Catalyzed Transformations and Understanding Their Underlying Mechanisms

Abstract: Hydrofunctionalizations are an attractive method for functionalizing olefins, forging new bonds in an atom-economic and sustainable fashion. We developed a variety of Rh–H catalysts that can couple heteroatom nucleophiles with olefin coupling partners.. In the first example, we developed an intermolecular anti-Markovnikov hydroamination of 1,3-dienes to form homoallylic amines. In the second example, we developed a divergent hydrothiolation of cyclopropenes.

Stereoselective Hydrofunctionalization of Unsaturated Hydrocarbons

Abstract: Hydrofunctionalization, which is defined as the addition of a hydrogen atom and another fragment to a degree of unsaturation, is an attractive method for transforming unsaturated hydrocarbons to value-added molecules. We developed Rh-, Pd-, and Cu-H catalysts that are capable of coupling both heteroatom and carbon nucleophiles to unsaturated hydrocarbons.

The Dihydro-β-agarofurans: Synthesis of the AB-Ring Core and Strategy/Method Development

Abstract: The research described herein focuses on the development of novel methods and synthetic sequences to solve problems in organic synthesis. Chapter 1 details our work on an operationally simple method to synthesize furans and pyrroles in high yield from keto-oxetanes, a non-obvious, easily accessible 1,4-dicarbonyl surrogate.

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