PhD defenses.

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


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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