CAREER: Stereochemically-Flexible Polyol Synthesis

在这个由化学系化学合成计划和刺激竞争研究实验计划(EPSCoR)联合资助的项目中，爱荷华州立大学的Jason Chen教授正在开发制备复杂多氧分子的方法。陈教授正在开发的教育模块向当地高中生介绍有机化学在现代医学中的重要性。这项工作的更广泛影响包括合成有机化学的潜在进展，包括发现安装密集含氧立体中心阵列的新方法，以及鼓励高中生从事STEM职业。这些方法强调对氧原子位置的可调控制，以及同时引入多个氧原子的能力。该项目致力于利用灵活的立体化学来设置多个连续的醇类手性中心。关键反应是烯烃的对映选择性、有机催化、多加氧以及与α-含氧醛的亲核加成反应。这些反应相辅相成，有可能在两个步骤中产生最多五个连续的立体中心。用这些方法制备的多氧结构通常存在于具有有用生物学性质的分子中。

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.