The focus of our research program is the development of new organic reactions and their application to the synthesis of therapeutically important compounds. Our efforts are concentrated in several areas:

•Ìý ÌýÌýAllene ChemistryÌýÌý – Allenyl aldehydes and esters are emerging as valuable intermediates in complex total synthesis especially due to their close association of three functional groups and axial chirality. In this aspect of our research, we utilize inexpensive organo-manganese reagents as auxiliaries to facilitate enantio- and diastereoselective reactions in allene synthesis.ÌýÌýWe are then fully utilizing theseÌýallenes as building blocksÌýin the synthesis of natural products. We have also employed other mechanistically-inspiredÌýapproaches to prepare other highly functionalized allenes.

•Ìý ÌýÌýNew Reactions with AlkynesÌýÌýÌý – In this project, we explore the reactivity of non-conjugated alkynes in the presence of ammonium salts. These non-metal catalysts promote cyclization reactions to affordÌýmedicinally important heterocycles under mild conditions, most likely through a novel ammonium/alkyne cation-pi interaction, which is also being investigated.

•Ìý ÌýÌýNucleophilic FluorinationÌýÌýÌý - We are designing new reactions to facilitate radiolabeling with F18 for medical imaging applications (PET). In this regard, we have taken several approaches including the use of chelating leaving groups pioneered in our group that we have termed Nucleophile Assisting Leaving Groups (NALGs). We are also developing novel crown ether-based phase transfer agents that serve as nucleophilic catalysts for various radiofluorination reactions.

•ÌýÌý One of ourÌýÌý Ìýis commercially available at Sigma-Aldrich.

•ÌýÌýÌýFor a less technical description of projects in the group,Ìý.

Affiliations

Center for Molecular Biology and Biotechnology