This research project is focused on the development of titanium-mediated (silyloxy)enyne cyclizations and a two-step subunit coupling based on Kulinkovich cyclopropanation / cyclopropanol opening. The application of these new methods to complex molecule synthesis will be demonstrated by total syntheses of amphidinolide J and spirolaxine. Multistep synthesis will be used as a platform for the introduction of new material into the undergraduate and graduate organic chemistry curriculum. In order to better convey the principles, excitement, and significance of multistep organic synthesis to students, web-based learning tools will be developed and lecture visits by industrial scientists will be organized.
With the support of this CAREER award from the Organic and Macromolecular Chemistry Program, Professor Andrew J. Phillips, of the Department of Chemistry and Biochemistry at the University of Colorado - Boulder, is developing new methods for the synthesis of complex organic molecules. The pursuit of this research plan is underpinned by the importance of further methodological and strategic advances in organic synthesis. Advances in this area will represent a fundamental contribution to the field of organic synthesis, and ultimately such advances have a broader impact on society in diverse ways such as providing improved/cheaper medicines, agrochemicals, and materials. Strategic advances in reaction design and efficiency can also result in substantially decreased pollution and resource expenditure. Professor Phillips will enhance the organic chemistry curriculum at both the undergraduate and graduate levels through a multi-dimensional approach involving the introduction of new and relevant course content, the development of web-based learning tools, and the initiation of lecture visits by industrial scientists.