New Reactions and Strategies in Synthesis

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The focus of this research involves the development of new methods in synthetic chemistry, and the subsequent application of the methodology to complex synthetic problems. This includes the development of the chemistry of tert-butyldimethylsilylhydrazones (TBSHs) for the synthesis of gem-dihalides, vinyl halides, hydrocarbons, diazo compounds, halogenated TBSHs, esters, ethers, and cyclopropane derivatives, and a directed condensation reaction to form mixed azines. Investigation to study new chemistry of mixed azines with the goal of developing a catalyzed process for the extrusion of dintrogen to form olefinic products is planned. Novel methodology directed toward a direct and generalizable enantioselective synthesis of quaternary carbon centers will be developed. In related work, a method for establishing vicinal carbon centers in a stereocontrolled manner will also be pursued. Studies to further develop a palladium-catalyzed decarboxylative coupling of arene carboxylates and its extension toward a protio-decarboxylation process as well as coupling reactions will be investigated. A convergent, enantioselective synthesis of the cytochalasins will be achieved suitable for the preparation of members of the class with widely variant macrocyclic substitution. A synthesis of the novel, nominally aromatic hydrocarbon bicyclopentadienylene will be completed and a study made of the chemistry of this theoretically interesting and thus far elusive molecule.With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. Andrew G. Myers in the Department of Chemistry and Chemical Biology at Harvard University. Dr. Myers will focus his work on developing synthetic methodology that can be applied to complex synthetic problems. The broader impact of the work is in the areas of pharmaceutical, agricultural and materials chemistry. Further, the project presents an excellent setting for the training of graduate students.