Development and application of metal catalyzed transfer hydrogenative C-C bond forming reactions
| dc.contributor.advisor | Krische, Michael J. | en |
| dc.contributor.committeeMember | Martin, Stephen F | en |
| dc.contributor.committeeMember | Dong, Guangbin | en |
| dc.contributor.committeeMember | Brodbelt, Jennifer S | en |
| dc.contributor.committeeMember | Kerwin, Sean M | en |
| dc.creator | Waldeck, Andrew Robert | en |
| dc.date.accessioned | 2016-08-23T20:37:38Z | |
| dc.date.available | 2016-08-23T20:37:38Z | |
| dc.date.issued | 2016-05 | |
| dc.date.submitted | May 2016 | |
| dc.date.updated | 2016-08-23T20:37:38Z | |
| dc.description.abstract | While polyketides display a diverse range of biological properties and are used extensively in human medicine, a lack of methods for the concise preparation of these complex structures still poses a significant challenge in the field of synthetic organic chemistry. To address this issue, metal catalyzed methods for transfer hydrogenative C-C bond formation have been developed. These methods construct products of carbonyl addition through direct C-H bond functionalization, which provides a more atom economic and efficient approach to carbonyl addition products and circumvents the need for stoichiometric use of chiral auxiliaries, premetallated C-nucleophiles, and discrete alcohol-to-carbonyl redox reactions. Efforts have been focused on the development of ruthenium-catalyzed coupling reactions of secondary alcohols to basic chemical feedstocks as well as the application of iridum-catalyzed couplings of primary alcohols with π-unsaturates in the context of the total syntheses of (−)-cyanolide A and (+)-cryptocaryol A. These total syntheses represent the most concise route reported to date for each natural product and illustrate the synthetic utility of transfer hydrogenative C-C bond forming methodology. | en |
| dc.description.department | Chemistry | en |
| dc.format.mimetype | application/pdf | en |
| dc.identifier | doi:10.15781/T2VH5CJ32 | en |
| dc.identifier.uri | http://hdl.handle.net/2152/39609 | en |
| dc.subject | Catalysis | |
| dc.subject | Spirolactone | |
| dc.subject | Total synthesis | |
| dc.subject | Cyanolide | |
| dc.subject | Cryptocaryol | |
| dc.title | Development and application of metal catalyzed transfer hydrogenative C-C bond forming reactions | en |
| dc.type | Thesis | en |
| dc.type.material | text | 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 |