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
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.