SusChEM: Beyond Acylation: New Methodology and Mechanistic Studies of Anhydrides for Stereoselective Synthesis

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With this project, Prof. Jared Shaw of the University of California, Davis, funded under the Sustainable Chemistry, Engineering, and Materials (SusChEM) initiative (Chemical Synthesis Program, Chemistry Division), seeks to develop new strategies for assembling complex organic molecules in ways that maximize sustainability. Laboratory experiments will take advantage of the predictive power of computational chemistry in the design and development of new reactions. This project will enable the synthesis of organic molecules that might eventually become new medicines or other materials with useful properties while minimizing the negative impacts on the environment associated with many current techniques. This project is centered on harnessing the potential of anhydrides to act as nucleophiles and to enable the synthesis of complex organic molecules with few byproducts. These transformations contribute to sustainability by occurring under mild conditions either in the absence of additional reagents or with the assistance of an organocatalyst, which serves as a benign alternative to transition metal-based catalysts. The ability of these new transformations to produce new organic architectures will be demonstrated in the construction of natural products derived from the Gelsimium species of plant. Natural products provide an over-riding theme for both research and outreach in this project. In addition to being an end-goal of the research, demonstrations of the properties of chemicals from plants as medicines enables this research to connect with the general public on many levels. Natural product-centered outreach includes an annual Science Café to engage the general public, field trips for local high school students to the UC Davis Arboretum, and participation in an annual Chemistry Camp for Blind and Visually Impaired (BVI) junior high and high school students.