Project Title: Concise Synthesis of N-Boc-2,3-methanoproline Methyl Ester
Student: Alexander Landgraf ’16
Mentor: Dr. Mark Mitton-Fry

Conformational rigidification through the incoporation of bicyclic ring systems constitutes a useful strategy for elucidating structure/function relationships. A two-step synthesis of a fully protected proline derivative, N-Boc-2,3-methanoproline methyl ester, has been accomplished via an intramolecular ring-closing reaction. The racemic product was readily separated using chiral supercritical fluid chromatography.  Additional studies using diastereo- and enantiopure reactants were conducted to establish the stereospecificity of this approach, thereby providing insight into the underlying reaction mechanism.

Contact Info


Merrick Hall
65 S. Sandusky St.
Delaware, OH 43015
P 740-368-3880

David Markwardt, Associate Dean of the OWU Connection