The focus of this research will be to explore the chemistry of cyclopentadienones as a new approach to biaryl synthesis. The concept will be tested by applying it to the synthesis of the alkaloid hippadine, and the related compound kalbretorine. The conjugate addition chemistry of cyclopentadienones will be explored by application to the synthesis of guanacastepene A, a hydroazulene based terpenoid. Further, a new oxidative cyclization of N-hydroxyethylpyrrolidines, in which the substrate is converted stereospecifically to an oxazoline by treatment with trimethylamine-N-oxide in the presence of an iron carbonyl catalyst, will be examined.
With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. Anthony J. Pearson in the Department of Chemistry at Case Western Reserve University. Professor Pearson will focus his work on the use of cyclopentadienones in the context of the total synthesis of important natural products. Oxidative cyclization reactions will also be developed for the synthesis of heterocycles. The work has potential for broader impact in the pharmaceutical industry and the project serves as an excellent venue for the training of undergraduates and graduate students and postdoctorals in the area organometallic chemistry applied to organic synthesis.
