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Synthetic approach to epibatidine from 1-(phenylsulfonyl)pyrrole

VanNess, Brandon G.
http://rave.ohiolink.edu/etdc/view?acc_num=wright1183494979

Abstract Details

2007, Master of Science (MS), Wright State University, Chemistry.
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.
Daniel Ketcha (Advisor)
88 p.
Chemistry, Organic
epibatidine; Diels-Alder; pyrrole

Recommended Citations

Citations

  • VanNess, B. G. (2007). Synthetic approach to epibatidine from 1-(phenylsulfonyl)pyrrole [Master's thesis, Wright State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=wright1183494979

    APA Style (7th edition)

  • VanNess, Brandon. Synthetic approach to epibatidine from 1-(phenylsulfonyl)pyrrole. 2007. Wright State University, Master's thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=wright1183494979.

    MLA Style (8th edition)

  • VanNess, Brandon. "Synthetic approach to epibatidine from 1-(phenylsulfonyl)pyrrole." Master's thesis, Wright State University, 2007. http://rave.ohiolink.edu/etdc/view?acc_num=wright1183494979

    Chicago Manual of Style (17th edition)

wright1183494979
1,158
© 2007, all rights reserved.
This open access ETD is published by Wright State University and OhioLINK.