Mentor: Dr. William P. Malachowski
Enantioselective Synthesis of Bicyclic Rings with Quaternary Centers via multiple approaches
In medicinal chemistry, the total syntheses of molecules that resemble natural products, with important biological activities to be used as drugs have been the major goal sought after by generations of chemists. The goal of this research project is to synthesize compounds that have a bicyclic ring system with quarternary centers from benzoic acid under highly stereo-controlled conditions. The proposed scheme for the synthesis is via several reactions (scheme 1), notably the Birch reduction-alkylation, Ruthenium-catalyzed olefin metathesis and Rauhut-Currier reaction. Earlier research results have shown positive sign of product formation but have yet to successfully produce an enantiomerically pure compound. The original scheme may be revised gradually with regards to the current progress of the research project.
If successfully synthesized, the stereospecific structure can be developed further to create drug-like molecules with biological activities. This synthesis is an important step that will give us new tools and important materials for the total synthesis of several target complex structures.