Studies towards the asymmetric total synthesis of solandelactone oxylipins: the total synthesis of solandelactone E
| dc.contributor.advisor | Martin, Stephen F. | en |
| dc.creator | Davoren, Jennifer Elizabeth | en |
| dc.date.accessioned | 2008-08-28T23:04:08Z | en |
| dc.date.available | 2008-08-28T23:04:08Z | en |
| dc.date.issued | 2006 | en |
| dc.description | text | en |
| dc.description.abstract | A stereocontrolled approach to the elaborate skeleton of the solandelactone oxylipins culminating in the total synthesis of solandelactone E in 26 steps and 0.7% overall yield from commercially available D-glyceraldehyde acetonide has been successfully developed and executed. Highlights of the synthesis include a novel diastereoselective, acetal directed cyclopropanation of an electron deficient olefin, a diastereoselective asymmetric dihydroxylation, and a stereoselective [2, 3]-sigmatropic rearrangement of a chiral selenoxide intermediate. This innovative route can be easily adapted to gain access to other oxylipins of differing carboskeletal framework. | |
| dc.description.department | Chemistry and Biochemistry | en |
| dc.description.department | Chemistry | en |
| dc.format.medium | electronic | en |
| dc.identifier | b65008091 | en |
| dc.identifier.oclc | 123355519 | en |
| dc.identifier.uri | http://hdl.handle.net/2152/2709 | en |
| dc.language.iso | eng | en |
| dc.rights | Copyright is held by the author. Presentation of this material on the Libraries' web site by University Libraries, The University of Texas at Austin was made possible under a limited license grant from the author who has retained all copyrights in the works. | en |
| dc.subject.lcsh | Lactones--Synthesis | en |
| dc.title | Studies towards the asymmetric total synthesis of solandelactone oxylipins: the total synthesis of solandelactone E | en |
| dc.type.genre | Thesis | en |