Oxygenated Carbenoids for Stereospecific Reagent Controlled Homologation

该奖项是根据2009年美国复苏和再投资法案（公法111-5）资助的。支持的研究将建立在早期的发现有关的立体定向试剂控制同系物（StReCH）的硼酸酯衍生物的对映体富集的主组手性卡宾。StReCH能够实现立体化学复杂分子的可编程迭代合成，但迄今为止，这种方法仅成功地证明了多烷基化材料的制备。将开展旨在扩大StReCH范围的研究，以涵盖多氧分子的合成。在追求这一奋进，两种类型的scalemic类卡宾物种能够引入氧化将被调查：α-金属化环氧乙烷和α-金属化S，O-缩醛。将探索产生这些敏感的有机金属试剂的新方法，并将使用它们的基于StReCH的过程战略性地部署在代表性生物碱和聚酮化合物天然产物的全合成中。俄勒冈州州立大学化学系的Blakemore说。Blakemore教授的研究重点是发展新的方法和概念，以实现立体控制的有机合成。通过开发促进分子构建的工具，该研究最终将通过加速生物活性剂和其他潜在有用的碳基材料的发现而使整个社会受益

This award is funded under the American Recovery and Reinvestment Act of 2009 (Public Law 111-5). The supported research will build on earlier discoveries concerning the stereospecific reagent controlled homologation (StReCH) of boronic ester derivatives by enantioenriched main group chiral carbenoids. StReCH enables a programmable iterative synthesis of stereochemically complex molecules, but to date this methodology has only been successfully demonstrated for the elaboration of polyalkylated materials. Studies designed to widen the scope of StReCH to encompass the synthesis of polyoxygenated molecules will be undertaken. In pursuing this endeavor, two types of scalemic carbenoid species capable of introducing oxygenation will be investigated: alpha-metallated oxiranes and alpha-metallated S,O-acetals. New methods for the generation of these sensitive organometallic reagents will be explored and StReCH based processes employing them will be strategically deployed for the total synthesis of representative alkaloid and polyketide natural products.With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Professor Paul R. Blakemore of the Department of Chemistry at Oregon State University. Professor Blakemore's research efforts focus on the development of new methods and concepts for the achievement of stereocontrolled organic synthesis. By targeting the development of tools that facilitate molecule building, the research will ultimately benefit society at large by speeding the discovery of biologically active agents and other potentially useful carbon based materials