CAREER: Stereochemically-Flexible Polyol Synthesis

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In this project jointly funded by the Chemical Synthesis program of the Chemistry Division and the Experimental Program to Stimulate Competitive Research (EPSCoR), Professor Jason Chen of Iowa State University is developing methods to prepare complex polyoxygenated molecules. Educational modules in development by Professor Chen introduce local high school students to the importance of organic chemistry in modern medicine. The broader impacts of this work include potential advances in synthetic organic chemistry from the discovery of new methods to install dense arrays of oxygen-containing stereocenters and the encouragement of high school students to pursue STEM careers.The methods emphasize tunable control over the placement of the oxygen atoms and the ability to introduce multiple oxygen atoms at the same time. This project focuses on setting multiple contiguous alcohol chiral centers with flexible stereochemistry. The key reactions are enantioselective, organocatalytic, polyoxygenation of enals and nucleophilic addition to alpha-oxygenated aldehydes. These reactions complement each other and can potentially deliver up to five contiguous stereocenters in two steps. The polyoxygenated structures prepared by these methods are commonly found in molecules with useful biological properties.