Oxygenated Carbenoids for Stereospecific Reagent Controlled Homologation

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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