Publication Date
2007
Document Type
Thesis
Committee Members
Daniel Ketcha (Advisor)
Degree Name
Master of Science (MS)
Abstract
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 2-chloro-5-iodopyridine was set as a synthetic goal and accomplished. The Diels-Alder reaction required further investigation to determine the extent to which 1-(phenylsulfonyl)pyrrole would undergo cycloaddition with dimethyl acetylenedicarboxylate and tosylacetylene. Once this was completed, the Diels-Alder reaction of 1-(phenylsulfonyl)-3-[5-(2-chloropyridyl)]pyrrole was attempted with tosylacetylene but the desired cycloadduct could not be found.
Page Count
88
Department or Program
Department of Chemistry
Year Degree Awarded
2007
Copyright
Copyright 2007, all rights reserved. This open access ETD is published by Wright State University and OhioLINK.
