The Aza-variant of the Photochemical Oxa-di-pi-methane Rearrangement for the Synthesis of Alkaloids

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The focus of this research is the development of the aza-variant of the oxa-di-pi-methane photochemical rearrangement as a new synthetic method for the preparation of nitrogen heterocycles. The rearrangement of azabicyclo[2.2.2]-octenones and azabicyclo[3.2.2]-nonenones is expected to provide tricyclic products in which the 3-member ring can be cleaved stereoselectively to give pyrrolizidines, indolizidines or tropanes. New methodologies based on the Diels-Alder reaction are being developed to synthesize the requisite photoprecursors and the attachment of photoprecursors and photosensitizers to resins will be explored as a means for ready isolation and functionalization of photoproducts. With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. Cynthia K. McClure of the Department of Chemistry at Montana State University. Professor McClure will focus her work on developing photochemical methods for the production of nitrogen heterocycles. The synthetic targets are compounds with interesting biological properties and the work should have broader impact in the pharmaceutical industry. The research provides an excellent training ground for the education of undergraduate and graduate students.