Steroids are a class of complex organic compounds that share a common carbon backbone consisting of four fused rings. Typically, medicinal steroids are synthetically prepared via modifications of naturally abundant steroids that are isolated from plants, animals, and fungi. The Shea lab is developing an intramolecular tandem Diels-Alder/Pauson-Khand strategy for the one-pot synthesis of tetracyclic steroid cores from acyclic tetraenynes. In this proposed reaction a cobalt-complexed alkyne will be used to convert an acyclic tetraenyne into a tetracyclic steroid core in one step. Currently, members of the Shea lab have been working on the synthesis of the desired acyclic tetraenyne precursor. We hope to communicate these synthetic efforts and share proposed modifications of the existing synthetic route to optimize the yield of the desired precursor. Additionally, to ensure the success of our one-pot strategy, we need to confirm that the cobalt-complexed alkyne does not hinder the Diels-Alder reaction. We have designed a kinetic NMR study to investigate the effect of cobalt-complexed alkynes on the rate of Diels-Alder reactions and hope to share these results as well.
A poster deriving from Special Studies with Kevin Shea, Professor of Chemistry.