Simplifying Complex Molecule Synthesis and Functionalization

The most powerful transformations in the synthesis of complex molecules generate significant structural complexity from simple precursors. In many cases, however, there is no practical approach available to translate intuitive retrosynthetic disconnections of a given target from the blackboard to the lab. This presentation will highlight strategies that address such challenges toward the synthesis and functionalization of bioactive complex molecules. These developments include a late-stage dimerization reaction applied to the total synthesis of the natural product himastatin, site-selective C??"H borylation reactions of saturated heterocycles, and stereoselective glycosylation reactions of minimally protected sugars. Complex mechanistic questions concerning the fundamental reactivity and bioactivity of these molecules will be addressed throughout. About the Speaker: Kyan D’Angelo is an NIH postdoctoral fellow in Prof. John Hartwig’s lab at the University of California Berkeley. He is from Toronto, Canada and completed his undergraduate studies in chemistry and biochemistry at the University of Toronto in 2014. He went on to obtain a master’s degree in chemistry at the same institution with Prof. Mark S. Taylor, where he focused on organoboron-catalyzed glycosylation reactions for the synthesis of oligosaccharides and glycolipids. He then joined Prof. Mohammad Movassaghi’s group at the Massachusetts Institute of Technology, where he completed his PhD in 2022. During that time, he developed a biogenetically inspired total synthesis of the antibiotic natural product himastatin and studied its bioactivity. His current research focuses on transition metal-catalyzed borylation reactions for the functionalization of strong C??"H bonds.

Speaker: Kyan A. D'Angelo, UC Berkeley