Making the Complex Simple: Exploring New Amine Chemical Space via Unusual Reactive Intermediates

Seminar | November 5 | 11 a.m.-12 p.m. | 120 Latimer Hall

 Jen Schomaker, Department of Chemistry, University of Wisconsin Madison

 College of Chemistry

The need for efficient access to molecules of importance to human health drives the development of innovative synthetic methods. Our group has had a long-standing interest in exploring stereochemically complex molecular space not well-represented in typical drug screening libraries. This had led to new methods to transform simple precursors into densely functionalized amines, azetidines, pyrrolidines, piperidines and amine-bearing carbocycles to speed the identification of novel amine chemical space with useful bioactivity. This talk will discuss strategies to harness the unique reactivity of unusual intermediates (methyleneaziridines, aziridinium ylides, 2-amidoallyl cations) accessed from allenes, alkenes, and 1,3-dienes, for the stereocontrolled syntheses of diverse N-heterocycles and amine-bearing carbocycles. The versatility of our methods is highlighted by the syntheses of analogs of jogyamycin, an aminocyclopentitol natural product with potent anti-malarial activity, and the identification of other amine scaffolds with promising biological activities.