| dc.contributor.advisor |
Krische, Michael J. |
| dc.creator |
Jones, Regan Andrew
|
| dc.date.accessioned |
2009-09-03T21:02:55Z |
| dc.date.available |
2009-09-03T21:02:55Z |
| dc.date.created |
2009-05 |
| dc.date.issued |
2009-09-03T21:02:55Z |
| dc.identifier.uri |
http://hdl.handle.net/2152/ETD-UT-2009-05-16 |
| dc.description.abstract |
The iridoids are a large family of monoterpenoid natural products that possess a wide range of biological activities. A great deal of research has already been done in the field of iridoid total synthesis, but limitations still remain. Specifically, few syntheses of iridoid β-glycosides have been reported. This work describes the 14 step asymmetric total synthesis of the iridoid β-glycoside (+)-geniposide utilizing a phosphine-catalyzed [3+2] cycloaddition as the key step. Other noteworthy steps in the synthesis include a palladium-catalyzed kinetic resolution and a previously unutilized method for iridoid glycosidation. In addition to describing the synthesis of (+)-geniposide, this dissertation will also review 1) phosphine-catalyzed cycloaddition reactions and 2) previous enantioselective total syntheses of iridoid glycosides. |
| dc.format.mimetype |
application/pdf |
| dc.language.iso |
eng |
| dc.subject |
Phosphine, Catalysis, [3+2] Cycloaddition, Synthesis, Iridoids
|
| dc.title |
The asymmetric total synthesis of (+)-geniposide via phosphine-catalyzed [3+2] cycloaddition |
| dc.contributor.committeeMember |
Magnus, Philip D. |
| dc.contributor.committeeMember |
Liu, Hung-wen |
| dc.contributor.committeeMember |
Martin, Stephen F. |
| dc.contributor.committeeMember |
Kerwin, Sean |
| dc.description.department |
Chemistry and Biochemistry
|
| dc.type.genre |
Thesis |
| dc.type.material |
text |
| thesis.degree.department |
Chemistry and Biochemistry
|
| thesis.degree.discipline |
Chemistry and Biochemistry |
| thesis.degree.grantor |
The University of Texas at Austin |
| thesis.degree.level |
Doctoral |
| thesis.degree.name |
Doctor of Philosophy |
