Our research encompasses structural, synthetic, medicinal, and functional organic chemistry. These synthetic activities are aimed at developing new procedures and transformations, particularly intramolecular cyclizations of general utility. Various pericyclic reactions, annulations, and cyclizations are under study. These investigations serve as a framework for the development of general methods and strategies for the total synthesis of natural products, compounds with medicinal promise, organic materials for thin film organic semiconductors and eventually solar cells.

       Organometallic chemistry is an important component of our research particularly palladium, copper, magnesium, and indium reagents. We have developed multi-component coupling protocols, particularly based on the carbometalation of propargyl alcohols for diverse targets. Thiovioxx and Tamoxifen mimics and stereoselective assembly of the ABC ring of the Taxol core by a carbometallation-intramolecular cycloaddition-ring closing metathesis strategy. Our organometallic chemistry has attracted considerable interest. Schreiber (Harvard) has used our indium chemistry to make 29,000 compounds, Merck is using out multi-component magnesium strategy to scale up one of their drug candidates, others have adopted our protocols for acetylene based palladium and copper coupling.

Synthesis of Taxol analogues:

Our stereoselective route to (Z)-Tamoxifen:

       Vinigrol is attracting world wide attention due to its ability to arrest formation of the AIDS complex. It also functions as a powerful tumor necrosis factor antagonist. Its unique structure is a challenging, significant target. We are developing two different strategies to the tricyclic skeleton which contains an eight membered ring using our indium chemistry. We are also developing a one pot alkyation-intramolecular Diels-Alder-Ring opening metathesis-Ring closing metathesis combination to triquinanes. We believe this can be extended to tetraquinanes with an additional ring closing metathesis step.

       Another interest is the design and synthesis of eneyne bridged cyclophanes with helical chirality in both the carbocyclic and heterocyclic series. We have also recently completed the first asymmetric synthesis of an acetylenic allenophane. These cyclophanes should possess interesting properties and are chiral as a result of the allenes. We have synthesized the first organic solvent soluble 2,9-substituted pentacenes for organic thin film semiconductors that may be deposited by inkjet printing. This is a novel platform for significant future research. We are extending our acene platforms for solar cells and developing a novel synthesis of Buckyball (C60). In total these interrelated studies provide new methods for the preparation of diverse systems of fundamental academic and industrial interest and contribute to our understanding of organic chemistry

Cyclophanes possessing helical chirality we have synthesized:

Our asymmetric synthesis of the first allenophane:

Our approach to a rational synthesis of C60: