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.