Concise Total Syntheses of Helifolenals A–D and Progress Towards Illihenin A

Abstract: 

Illicium sesquiterpenes showcase diverse polycyclic scaffolds and complex oxygenation patterns. In pursuit of an illicium natural product called illihenin A, total syntheses of helifolenals A–D were achieved. I will share my unpublished work on enantiospecific syntheses of helifolenals A–D featuring an intramolecular Diels–Alder reaction and discuss a biomimetic strategy to illihenin A.

Analytical chemistry tools revealing complex organismal metabolism

Analytical chemistry tools, such as mass spectrometry, have been increasingly used to answer complex biological questions. For example, metabolomics and stable isotope tracing have revealed key biological molecules and their fluxes in both healthy and diseased conditions, providing potential drug targets. In this seminar, we will discuss how these techniques are used to discover novel biologically important molecules that organisms utilize to maintain whole-body metabolic homeostasis.

Electrophilic Cyclization Reactions: Mechanism-Inspired Methods Development

Abstract: 

Electophilic cyclizations are common reactions to form substituted heterocycles. Here investigations into two systems and the mechanistic findings are presented. In the first part haloboration versus cyclization is explored. Haloboration was found to be reversible and could be intercepted to form zwitterionic sulfonium borates which were analyzed by NMR spectroscopy and X-ray crystallography.