Development of Pummerer-Based Oxidative Cyclization Chemistry for Natural Products Synthesis

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The focus of this research is concerned with developing methods for the preparation of 3,3-spirocycle-heterocycle and related systems by the use of the Pummerer oxidative rearrangement. Specific targets include 3,3-spyrocyclic oxindole, 3,3-spirocyclic benzofuranone, 5,5-spirocyclic oxazolidinone and 5,5-spirocyclic imidazolinone. These compounds serve as models for the preparation of a large number of natural products having interesting biological properties.With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. Ken S. Feldman of the Department of Chemistry at Pennsylvania State University. Professor Feldman will focus his research efforts on developing synthetic applications of selective oxidative cyclization. In this way, the body of knowledge on heterocyclic oxidative cyclization chemistry will be augmented and using the methodology, syntheses of model compounds for the preparation of natural products will be carried out. The project has broader impacts for the pharmaceutical industry and, will afford an excellent venue for the training of undergraduates, some from underrepresented minority groups, and graduate students.