As many bioactive molecules from natural products contain quaternary carbons, the development of new therapeutic treatments is dependent on the synthesis of molecules which exhibit this property. Due to the increasing need of new drug candidates, the main goal of our research is to develop an approachable, enantioselective synthesis pathway for tricyclic structures containing quaternary carbons, which affords high yields while using readily available, inexpensive starting materials. In our previous experimental work, the synthesis of these structures was achieved in four steps. As a first step, the Birch reductive alkylation of benzoic acid was used to create a quaternary stereocenter. The product of this reaction was then advanced along several pathways to construct a range of cyclohexadiene aryl triflate substrates for the key enantioselective transformation: an intramolecular Mizoroki-Heck cross coupling reaction, which affords tricyclic structures with quaternary stereocenters. Future studies will focus on achieving the Mizoroki-Heck reaction in good yields and high enantioselectivity. By developing the most efficient and most stereoselective protocol, such reactions can be further explored with different substrates, affording more potentially therapeutic molecules.<br/>

Catalytic enantioselective Birch-Heck reaction sequence for the efficient generation of potentially therapeutic molecules

2019 Spring National Meeting

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