Open Access. Powered by Scholars. Published by Universities.®
Physical Sciences and Mathematics Commons™
Open Access. Powered by Scholars. Published by Universities.®
Articles 1 - 1 of 1
Full-Text Articles in Physical Sciences and Mathematics
Synthetic Approach To Epibatidine From 1-(Phenylsulfonyl)Pyrrole, Brandon G. Vanness
Synthetic Approach To Epibatidine From 1-(Phenylsulfonyl)Pyrrole, Brandon G. Vanness
Browse all Theses and Dissertations
The goal of this research was to synthesize the natural product epibatidine, a non-opiate analgesic and nicotinic acetylcholine agonist isolated from Epipedobates tricolor. A synthetic pathway utilizing a Diels-Alder cycloaddition of a 3-pyridyl substituted pyrrole and tosylacetylene was conceived based upon the original mass spectral fragmentation pathway of epibatidine determined by Daly. Although this pathway had been previously attempted using 1-(triisopropyl)-3-[5-(2-chloropyridyl)]pyrrole in the key Diels-Alder step, the lack of cycloadduct suggested that a pyrrole with a more electron withdrawing protecting group was required for this step. Therefore, synthesis of 1-(phenylsulfonyl)-3-[5-(2-chloropyridyl)]pyrrole via a palladium catalyzed cross-coupling reaction of 1-(phenylsulfonyl)-3-pyrroline and …