Synthesis of Spiro-Pyrrol-Aziridine as a Novel CNS-targeting Molecular Scaffold

Mentors: Jean-Charles Marié, Giovanni Muncipinto

The structure of the backbone on which a chemical compound is built – i.e. the “scaffold” – largely determines the compound’s properties, such as stability and reactivity. Therefore, in order to create drugs with various novel pharmaceutical properties, new scaffolds must be synthesized. Woody spent the summer synthesizing [5,3] spiro-pyrrol-aziridine, a compound with structural elements that give it a high likelihood of successfully passing through the blood-brain barrier, and thus targeting the central nervous system.

Because this compound was initially synthesized unexpectedly as a product of a previously performed reaction, Woody spent the summer re-creating the synthesis of [5,3] spiro-pyrrol-aziridine, and deducing the mechanism behind its synthesis. Woody successfully developed a synthesis route to synthesize this compound. In addition, by following the mass of intermediates in the reactions he used, Woody was able to determine the mechanism by which this compound is formed. With this increased understanding, Woody was also able to propose synthesis paths for many other stereoisomers of spiro-pyrrol-aziridine.



Woody, a senior at Concord Academy, synthesized chemical compounds containing spiro-pyrrol-aziridine, in hopes that they may have promise as drugs for CNS diseases.