Studies towards the total synthesis of condylacarpine and studies towards the enantioselective synthesis of (+)-methyl lysergate
| dc.contributor.advisor | Martin, Stephen F. | en |
| dc.creator | Deck, Jason Anthony | en |
| dc.date.accessioned | 2008-08-28T23:22:56Z | en |
| dc.date.available | 2008-08-28T23:22:56Z | en |
| dc.date.issued | 2007 | en |
| dc.description | text | en |
| dc.description.abstract | An iminium ion cascade sequence was designed and its implementation attempted to form the pentacyclic core structure of the natural product condylocarpine. Trapping of the transient Pictet-Spengler-type spiroindolenium ion with a latent nucleophile would form two of the five rings of condylocarpine in a regioselective manner. Progress towards the first fully stereocontrolled synthesis of a lysergic acid derivative has been described. The route utilizes intermediates with the appropriate oxidation state for the target, and the two stereocenters are installed via asymmetric catalysis. The d ring and second stereocenter were simultaneously formed via an unprecedented microwave heated asymmetric ring closing metathesis (ARCM). | |
| dc.description.department | Chemistry and Biochemistry | en |
| dc.description.department | Chemistry | en |
| dc.format.medium | electronic | en |
| dc.identifier | b68664308 | en |
| dc.identifier.oclc | 166353470 | en |
| dc.identifier.uri | http://hdl.handle.net/2152/3026 | 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 | Condylocarpine | en |
| dc.title | Studies towards the total synthesis of condylacarpine and studies towards the enantioselective synthesis of (+)-methyl lysergate | en |
| dc.type.genre | Thesis | en |