CAREER: Versatility of Phosphorothioate Esters in the Synthesis of Sulfur-Containing Molecules

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In this project, funded by the Chemical Synthesis program of the Division of Chemistry and the Office of Experimental Program to Stimulate Competitive Research, Jimmy Wu of Dartmouth College will explore novel methods for the synthesis of sulfur-containing molecules. This will be accomplished via two methods: 1) UV-promoted or gallium-catalyzed substitution of alcohols, ethers, silyl ethers, or benzoates, and 2) gallium-catalyzed hydrothiolation of unactivated alkenes. The second objective of this application is to demonstrate the utility of phosphorothioate esters in stereoselective syntheses of sulfur-containing molecules.Many well-known bioactive drugs such as antibiotics, anti-inflammatory agents, and anti-ulcerative agents, contain sulfur. Sulfur-containing compounds also play an important role in organic synthesis as they are useful intermediates in a wide range of reactions. Given the importance of sulfur in chemistry and biology, it is rather surprising that comparatively little effort has been devoted to this research area. This project seeks to develop new technologies for the preparation of this important class of compounds. A primary broader impact of this proposal includes increasing the awareness and knowledge of organic chemistry in the general population by creating a series of short, animated films which focus on central topics in organic chemistry. Through the integrated educational and research activities of this project, undergraduate and graduate students will receive training and be prepared for careers in either academia or industrial settings.