Green Synthesis of Pharmaceutically Pertinent Bicyclic Pyrrolidines using the Castagnoli-Cushman Reaction



Claire Borg, Michael Moilanen

Faculty Mentor(s)

Academic Service Learning in Public Health


The synthesis of nitrogen-containing cyclic compounds (commonly known as azaheterocycles or N-heterocycles) has constantly been of importance to pharmaceutical companies given that they have great beneficial biological activities. One of these N-heterocyclic motifs is the azadiquinane (two fused 5-membered rings bearing one nitrogen atom, such as Hadinecine; a muscle relaxer). In this proposal, a cost-saving approach to highly functionalized azadiquinanes, using a simple starting precursor will be explored. Two functional groups within the molecule will be joined through a process called intramolecular cross-coupling. Starting from an appropriately designed compound, which bears an alkene unit (double bonded carbon atoms) and an alcohol (OH-containing) functional group, this cross-coupling process will enable the formation of the desired product. The reactions are performed without expensive transition metal-catalysts and under mild conditions (e.g., at room temperature). The method is potentially inexpensive, stereoselective, and sustainable, thus, making it the most preferable to medicinal and environmental chemists. Through collaborations, the generated compounds will be screened for potential bioactivity and toxicity, with a strong focus on G-protein coupled receptors.

Keywords: Bicyclic Pyrrolidines, Castagnoli-Cushman, azaheterocycles, sustainability


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