Research Interests: Organic synthesis, medicinal chemistry, natural products, chemical biology.
Research in the Majireck group broadly aims to (1) develop new methods for synthesis of biologically active small molecules and (2) openly collaborate with the biomedical research community to identify small-molecule probes of human disease biology.
Exploration of unusual functional groups.
Functional groups that have been underexplored, typically due to the lack of viable synthetic procedures, provide fertile grounds for new reaction discovery and applications. The Majireck group is currently exploiting several recent methodologies from our laboratory that explore unusual functional groups for the development of new and useful reactions toward biologically important targets. For example, in earlier work we have leveraged the recent developments in Rh-catalyzed decomposition of N-sulfonyl-1,2,3-triazoles to generate neuroactive phthalan and/or phenethylamine structures with a versatile N-(1-alkoxyvinyl)sulfonamide moiety. This obscure but promising functional group has, until recently, been relatively unexplored. However, research by our group and others have transformed this subclass of compound into a valuable N,O-containing synthon for organic synthesis - a topic that our laboratory will publish a review on soon.
More recently, our lab has discovered >40 examples of, until recently, rare N-quaternized ketene N,O-acetals. These unusual constructs are currently being investigated as “trapped ketenium ion” reagents for a variety of purposes including cycloadditions and acid-catalyst free electrophilic aromatic substitutions. Alternatively, these species can also act as electrophiles in nucleophilic aromatic substitutions toward production of novel heterocycles. This exciting new area of research has been recently sponsored by Organic Syntheses, Inc. and the National Science Foundation.
Target-oriented synthesis and medicinal chemistry.
We are engaged in several total synthesis and medicinal chemistry campaigns, with the ultimate function-oriented synthesis goal of producing natural product-inspired drug leads, particularly for infectious disease. The following alkaloids and their derivatives are all present targets of ongoing research in our lab.
Collaborative Chemical Biology
In every project, we aspire to leverage our capabilities in organic synthesis to contribute toward our understanding of biology, particularly with regard to human diseases. To do this, we partner with a variety of collaborators. Recently, through sponsorship by the American Heart Association, we have joined collaborative projects in cardioactive peptide synthesis, molecular imaging, medicinal chemistry, and nanomedicine with the McCarthy Lab at Masonic Medical Research Institute in nearby Utica, NY.
Collaborative Liberal Arts
One of the greatest privilege's of working at a liberal arts institution is our frequent interaction with students and colleagues across not only STEM disciplines, but the arts in humanities. Though not prominently featured on this webpage, members of our group have actively engaged in projects and independent studies in Art, Philosophy, History, and Ethics. Doing so trains our students not only excel in technical science, but to think broadly and engage with complex societal problems. For example, we have recently assisted Assistant Professor of History Mackenzie Cooley to study historical uses of natural products in medicine.
