Cyclopropane-mediated Organic Synthesis

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The focus of this research is refinement of the Kulinkovich reaction which involves the titanium-mediated cyclopropanation of esters and the use of the resulting heteroatom-substituted cyclopropanes as synthetic intermediates for medium size ring formation. Methods for asymmetric cyclopropanation, cyclopropanol and cyclopropylamine-mediated syntheses, and the elaboration of vinylcyclobutanols will be pursued and a total synthesis of the natural product suberosenone will be used to highlight the methodology.With this renewal award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. Jin K. Cha of the Department of Chemistry at the University of Alabama. Professor Cha will focus his work on the development of methods for the stereoselective construction of carbocycles by taking advantage of the release of ring strain present in readily available heteroatom-substituted cyclopropanes. The research has potential broader impact in the pharmaceutical and agricultural industries and presents an excellent vehicle for the training of students.