03/14/19 - 9:45 AM to 11:00 AM
Department Seminar: Professor Carolyn E. Anderson
Synthesis of Highly Functionalized N-Alkyl 2-Pyridones and Indolizines
Over the past decade, our group has been highly successful in generating a new suite of reactions for the synthesis of unique chemical architectures containing N-alkyl 2-pyridones, beginning from simple 2-alkoxypyridine substrates 1. Amongst these new structures, β-iodo N-alkenyl pyridones 3 and α-(N-2-pyridonyl) ketones 4 are particularly important building blocks for the preparation of more complex pyridone targets, including isoquinoline alkaloids. Further, recent efforts have revealed that the same 2-propargyloxypyridines 1 can be converted directly into highly substituted indolizines 6 upon treatment with Au(I) in the presence of ketones. As with N-alkyl 2-pyridones, indolizines are a privileged scaffold found commonly within pharmaceutical targets in a wide range of therapeutic areas. Given the prevalence of the indolizine core, a method that allows for the rapid synthesis of highly substituted variants has the potential to make a significant impact on how these materials are prepared on industrial scale.
Thursday, March 14
Kate & Michael Bárány Conference Room (117/119 Smith Hall)
“Careers at primarily undergraduate institutions”
Professor Anderson’s research efforts involve developing facile methods for the synthesis and application of N-alkyl pyridones. N-Alkyl pyridones are interesting motifs due to their prevalence in natural products as well as their ability to serve as biological mimics in pharmaceutical targets. Projects in the group include: optimization of new organic and organometallic reactions, evaluation of reaction scope, and mechanistic studies.