Pyrrole as a Scaffold for Synthesis: Approaches to Stemona and Indolizidine Alkaloids.
Molecular Horizons Seminar - Associate Professor Jason Smith
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Wollongong
32.G01
Natural products featuring 5-membered nitrogen heterocyclic rings fused to at least one other ring are abundant in nature. Various approaches to the synthesis of these natural products have been reported, including a multitude of successful strategies involving key annulation reactions that exploit the reactivity of pyrrole. The presentation will describe the development of methods for the Brønsted acid mediated annulation of pyrroles featuring N-tethered α,β-unsaturated esters and ketones, and the application of these methods to total syntheses of the indolizidine alkaloids and the more complex Stemona alkaloids, including sessilifoliamides and dehydrostenines.