Fragmentations of bicyclic ketoesters and synthetic efforts toward eleutherobin
| dc.contributor.advisor | Rainier, Jon D. | en_US |
| dc.contributor.author | Xu, Qing | |
| dc.creator | Xu, Qing | en_US |
| dc.date.accessioned | 2013-04-11T08:40:49Z | |
| dc.date.available | 2013-04-11T08:40:49Z | |
| dc.date.issued | 2002 | en_US |
| dc.identifier.uri | http://hdl.handle.net/10150/279938 | |
| dc.description.abstract | An unprecedented anionic condensation, fragmentation, and elimination sequence from the coupling of bicyclo[2.2.1]heptenones with aldehydes is described. This reaction leads to the stereoselective formation of disubstituted five-membered rings which are present in a wide array of bioactive molecules. Oxabicyclo[2.2.1]heptenone 106 also undergoes two-carbon ring expansions when subjected to anionic conditions and Michael acceptors. As an outgrowth of this interesting chemistry, we have been able to access the carbon skeleton of oxygenated cembranoids by subjecting bis-activated ene-yne to the enolate from oxabicyclo[2.2.1]heptenone 106. In order to demonstrate the synthetic utility of the anionic condensation, fragmentation, and elimination reaction, we have applied it to the synthesis of nortetillapyrone. | |
| dc.language.iso | en_US | en_US |
| dc.publisher | The University of Arizona. | en_US |
| dc.rights | Copyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author. | en_US |
| dc.subject | Chemistry, Organic. | en_US |
| dc.title | Fragmentations of bicyclic ketoesters and synthetic efforts toward eleutherobin | en_US |
| dc.type | text | en_US |
| dc.type | Dissertation-Reproduction (electronic) | en_US |
| thesis.degree.grantor | University of Arizona | en_US |
| thesis.degree.level | doctoral | en_US |
| dc.identifier.proquest | 3050292 | en_US |
| thesis.degree.discipline | Graduate College | en_US |
| thesis.degree.discipline | Chemistry | en_US |
| thesis.degree.name | Ph.D. | en_US |
| dc.identifier.bibrecord | .b42723644 | en_US |
| refterms.dateFOA | 2018-06-27T08:38:29Z | |
| html.description.abstract | An unprecedented anionic condensation, fragmentation, and elimination sequence from the coupling of bicyclo[2.2.1]heptenones with aldehydes is described. This reaction leads to the stereoselective formation of disubstituted five-membered rings which are present in a wide array of bioactive molecules. Oxabicyclo[2.2.1]heptenone 106 also undergoes two-carbon ring expansions when subjected to anionic conditions and Michael acceptors. As an outgrowth of this interesting chemistry, we have been able to access the carbon skeleton of oxygenated cembranoids by subjecting bis-activated ene-yne to the enolate from oxabicyclo[2.2.1]heptenone 106. In order to demonstrate the synthetic utility of the anionic condensation, fragmentation, and elimination reaction, we have applied it to the synthesis of nortetillapyrone. |
