Studies toward the total synthesis of (–)-stolonidiol : a small molecule inducer of choline acetyltransferase
| dc.contributor.advisor | Siegel, Dionicio R. | en |
| dc.contributor.committeeMember | Magnus, Philip D. | en |
| dc.contributor.committeeMember | Kerwin, Sean M. | en |
| dc.contributor.committeeMember | Cowley, Alan H. | en |
| dc.contributor.committeeMember | Willson, Grant | en |
| dc.creator | Barton, Thomas John | en |
| dc.date.accessioned | 2012-07-06T18:32:54Z | en |
| dc.date.accessioned | 2017-05-11T22:25:40Z | |
| dc.date.available | 2012-07-06T18:32:54Z | en |
| dc.date.available | 2017-05-11T22:25:40Z | |
| dc.date.issued | 2012-05 | en |
| dc.date.submitted | May 2012 | en |
| dc.date.updated | 2012-07-06T18:33:29Z | en |
| dc.description | text | en |
| dc.description.abstract | The marine diterpene (–)-stolonidiol (1) has been shown to upregulate neuronal levels of acetylcholine. The mechanism through which a small molecule can impart this allosteric-like effect is currently unknown. A laboratory preparation of the natural product was undertaken in order to produce matieral for biological testing and elucidation of the unknown mechanism of action. During the course of this study, a tandem enyne-Suzuki reaction was investigated to form both rings of the fused bi-cyclic structure 26 in a single operation, but was met with undesired diastereoselectivity in the first cyclization step. The directing effect was found to be general on 1,6-homopropargyl enynes. Further efforts toward the molecule focused on an enantioselective formation of the cyclopentane core through an extension of a copper-mediated silylcyclization of epoxyalkyne 71. Using this intermediate two routes involving acrylate as a lynchpin to close the large ring were investigated. Additionally, a route designed to employ an intramolecular Knoevenagel condensation was explored to generate this ring system. | en |
| dc.description.department | Chemistry | en |
| dc.format.mimetype | application/pdf | en |
| dc.identifier.slug | 2152/ETD-UT-2012-05-5237 | en |
| dc.identifier.uri | http://hdl.handle.net/2152/ETD-UT-2012-05-5237 | en |
| dc.language.iso | eng | en |
| dc.subject | Diterpene | en |
| dc.subject | Total synthesis | en |
| dc.subject | Knovenagel | en |
| dc.subject | Acrylate lynchpin | en |
| dc.title | Studies toward the total synthesis of (–)-stolonidiol : a small molecule inducer of choline acetyltransferase | en |
| dc.type.genre | thesis | en |