Julia Nafso, FCLC 2024

MAJOR: Natural Sciences

BIO: Julia Nafso is a senior majoring in Natural Sciences as well as a concentration in Organismal Biology. After graduating, she aims to attend a dental school where she hopes to specialize in endodontics. In her free time, she is busy pursuing personal research in pediatric sleep apnea.

PROJECT TITLE: Ring Expansion of N-Benzyl Aziridines to 1,2,3,4-Tetrahydroisoquinolines

MENTOR: Dr. Martin J. Di Grandi, Department of Natural Sciences

ABSTRACT: This research project explores the use of N-benzyl aziridines as precursors to 1,2,3,4-tetrahydroisoquinolines, part of the core ring system of pancratistatin, a natural product with anti-cancer activity. Ultimately, we hope to develop sufficiently mild conditions that will allow the synthesis of pancratistatin. We demonstrated that subjecting highly oxygenated N-benzylaziridines to acids of varying strength was sufficient to effect a rearrangement that yields 1,2,3,4-tetrahydroisoquinolines. This modification has the potential to render the sequence enantioselective when effected with chiral sulfonic acids. Application of this ring expansion methodology to more highly functionalized N-benzylaziridines has defined milder reactions conditions, which can potentially render the reaction enantioselective.