Functionalization of C-aryl glycals and studies toward the total synthesis of 5-hydroxyaloin A
| dc.contributor.advisor | Martin, Stephen F. | |
| dc.creator | Procko, Kristen Jean | en |
| dc.date.accessioned | 2015-02-16T14:24:55Z | en |
| dc.date.issued | 2009-08 | en |
| dc.date.submitted | August 2009 | en |
| dc.date.updated | 2015-02-16T14:24:56Z | en |
| dc.description | text | en |
| dc.description.abstract | In the context of ongoing efforts toward C-aryl glycoside synthesis, a recently developed approach to form C-aryl glycals from 2-deoxysugar lactones was expanded to form novel substrates. This approach has been applied to the synthesis of various furyl glycals, allowing access to C-aryl glycals via a benzyne furan (4+2) cycloaddition methodology. The hydroboration-oxidation of said C-aryl glycals has allowed access to C(2)-oxygenated C-aryl glycosides via the benzyne cycloaddition approach. An approach to the total synthesis of 5-hydoxyaloin A is detailed, in which regioselective benzyne furan (4+2) cycloadditions were achieved via the use of a silicon tether. Two approaches to the anthrone core have been applied; one in which an unsymmetrically-substituted aryl ring is first constructed by means of a silicon tether, and one in which the unsymmetrically-substituted ring is formed last, also utilizing a silicon tether. The latter approach has allowed access to the anthrone core of 5-hydroxyaloin A, and only a final desulfurization remains in order to access the natural product. | en |
| dc.description.department | Chemistry | en |
| dc.format.mimetype | application/pdf | en |
| dc.identifier.uri | http://hdl.handle.net/2152/28464 | en |
| dc.subject | C-aryl glycoside | en |
| dc.subject | Glycal | en |
| dc.subject | Hydroboration-oxidation | en |
| dc.subject | Benzyne | en |
| dc.subject | Benzyne-furan cycloaddition | en |
| dc.subject | (4+2) cycloaddition | en |
| dc.subject | Furyl glycal | en |
| dc.subject | Silicon tether | en |
| dc.subject | 5-hydroxyaloin A | en |
| dc.subject | Regioselective cycloaddition | en |
| dc.subject | Aloe | en |
| dc.subject | Sulfide | en |
| dc.subject | Directed ring opening | en |
| dc.title | Functionalization of C-aryl glycals and studies toward the total synthesis of 5-hydroxyaloin A | en |
| dc.type | Thesis | en |
| thesis.degree.department | Chemistry | en |
| thesis.degree.discipline | Chemistry | en |
| thesis.degree.grantor | The University of Texas at Austin | en |
| thesis.degree.level | Doctoral | en |
| thesis.degree.name | Doctor of Philosophy | en |