Stereoselective Carbene Annulations for Assembling Complexity

Friday, March 8, 2019

Prof. Indrajeet Sharma

Department of Chemistry & Biochemistry

The University of Oklahoma

Reception: 3:00PM Hand 1135

Seminar: 3:30PM Hand 1144

Abstract: Natural products bearing complex structures have served as successful lead molecules in therapeutics development for centuries. More than half of the current drugs available today are either natural products or their derivatives. Despite dramatic advances in natural products-inspired drug discovery, many bioactive scaffolds (spirocycles, medium-sized rings, and terpene furanolactones) remain underexploited in probe and drug discovery owing to the lack of efficient and flexible synthetic routes. For example, the stereoselective installation of quaternary spiro-centers poses challenges in spirocycles synthesis, while entropy barrier in ring cyclization limits the synthetic access to medium sized (8–12 atoms) rings. To address these challenges, our group is utilizing diazo-derived metal carbenes, which are ambiphilic in nature, and offer the possibility of sequential reactions with a nucleophile and an electrophile, and are ideal for annulation reactions leading to the rapid generation of molecular complexity. This research has been funded through the NSF CAREER Award, ACS-PRF Doctoral New Investigator Grant, OCAST Health grant, NIDA-R21/R33 Award, and the NIGMS-COBRE funds.

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