Danheiser Research Group

Research in the Danheiser Laboratory focuses on the development of new synthetic methods and strategies, and their application in the total synthesis of natural products and biologically important compounds. A major thrust of the current research is the design and invention of new cycloaddition and annulation strategies for the synthesis of carbocyclic and heterocyclic compounds. Many of the methods under study involve the application of unusual molecules and highly reactive species as building blocks for the construction of important classes of organic compounds. We are particularly interested in the chemistry of highly unsaturated conjugated molecules, such as vinylketenes, iminoacetonitriles, conjugated enynes, and vinylallenes, and unusually strained molecules such as arynes, cycloalkynes, and cyclic allenes.

Current research in the laboratory falls into four broad areas. The main goal is the design and invention of new strategies for the synthesis of carbocyclic and heterocyclic compounds. In this area an important objective is the development of methods that can be applied to highly substituted systems that are difficult to construct using existing methodology. The application of the methods we develop as key steps in the total synthesis of natural products is another important component of our program. These studies serve to test and further refine our new reactions in the context of more complicated systems. The synthesis of molecules with unusual electronic properties constitutes another goal in the lab. Past research in this area has included the development of new methods for the synthesis of azulenes and oligoazulenes and novel polycyclic aromatic and heteroaromatic systems. Finally, the development of methods for environmentally benign synthesis (“Green Chemistry”) is another aim of our program. Past research in this area has included investigations of the utility of supercritical carbon dioxide as a reaction medium for organic synthesis.

The laboratory has pioneered the application of iminoacetonitriles as cycloaddition partners for the synthesis of several classes of nitrogen heterocycles. This chemistry has been applied in total syntheses of several neurotoxic alkaloids isolated from poison dart frogs.