Tools for harnessing atropisomerism in 1-aryl-β-carbolines

Tools for harnessing atropisomerism in 1-aryl-β-carbolines
Cristina Díaz ’25, Chemistry major
Malaquias Loiza ’26, Biochemistry major
Josef Crenshaw ’28, Biochemistry major
Brian Ladino ’28, Biochemistry major
Elizabeth Perda ’26, Biochemistry major
Alma Martinez ’26, Biochemistry major
Joseph Mazzucca ’25, Biochemistry major
John Stathoulopoulos ’26, Chemistry major
Faculty mentor: Dr. Seann Mulcahy, Chemistry and Biochemistry

Axially chiral molecules with high barriers to rotation are becoming increasingly more prominent in drug discovery, chemical biology, and materials science. We have shown that 1-aryl-β-carbolines exhibit high configurationally stability, with barriers to rotation greater than 30 kcal/mol and have recently disclosed an asymmetric synthesis of these molecules. In this presentation, we will describe three different projects involving undergraduate students at Providence College. These projects involve the discovery of new chemical reactions and probe molecules involving the β-carboline scaffold. First, we will describe our efforts to perform a kinetic resolution of these molecules by performing a peptide-catalyzed N-oxidation. Then, we will describe our efforts towards the synthesis of the atropisomeric natural product chaetogline F. Finally, we will describe a synthetic strategy toward a new class of biaryl N,P-ligands for asymmetric catalysis.

Poster Presentation: Wednesday, April 23, 11 a.m. – 12:30 p.m.