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Strategies towards the synthesis of prostaglandin analogues
Includes bibliographical references (leaves 173-179).
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| Main Author: | |
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| Format: | Thesis |
| Language: | English |
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Department of Chemistry
2014
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| _version_ | 1867613226166910977 |
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| access_status_str | Open Access |
| author | Haupt, Hayley Claire |
| author_browse | Haupt, Hayley Claire |
| author_facet | Haupt, Hayley Claire |
| author_sort | Haupt, Hayley Claire |
| collection | Thesis |
| description | Includes bibliographical references (leaves 173-179). |
| format | Thesis |
| id | oai:open.uct.ac.za:11427/6312 |
| institution | University of Cape Town (South Africa) |
| language | eng |
| last_indexed | 2026-06-10T12:32:46.693Z |
| license_str | Not specified — see source repository |
| provenance_str_mv | Harvested via OAI-PMH from UCTD — University of Cape Town Open Access Repository |
| publishDate | 2014 |
| publishDateRange | 2014 |
| publishDateSort | 2014 |
| publisher | Department of Chemistry |
| publisherStr | Department of Chemistry |
| record_format | dspace |
| source_str | UCTD — University of Cape Town Open Access Repository |
| spelling | oai:open.uct.ac.za:11427/6312 Strategies towards the synthesis of prostaglandin analogues Haupt, Hayley Claire Chemistry Includes bibliographical references (leaves 173-179). Different strategies for the synthesis of cyclopentenone prostaglandins and their analogues have been explored. The key transformation critical to the success of each of the described routes involves a Lewis-acid mediated retro Diels-Alder (rDA) reaction as the final step in liberating a 4, 5 disubstituted cyclopent-2-ene-1- one under extremely mild conditions. The first approach involves installation of the a-chain followed by base-mediated methodology to affect regiospecific enolate generation. Effective trapping of the enolate generates the requisite target. Within the context of this strategy both 2- and 3-component coupling protocols have been elaborated. Having demonstrated that the a- and p- sidechains could be installed, the key rDA reaction has been used to generate target analogues. The second approach utilizes a Diels-Alder cycloaddition reaction as the key step. The thermal and Lewis-acid catalysed Diels-Alder reactions between tricyclo[5.2.1.0 2,6]dec-8-en-3-one and 3-hydroxytricyclo[5.2.1.0 2,6]dec-8-ene with butadiene and butadiene sulfone have been investigated. While reaction between the enone and the dienophiles proved to be low yielding, the reaction between the allylic alcohol and butadiene sulfone proceeded readily and in high yield. The derived cycloadduct represents a late-stage intermediate for the synthesis of isoprostanes. Methodologies to perform cis-hydroxylation followed by oxidative cleavage of the cyclohexene moiety have been successfully implemented. Finally, a synthesis was designed for generating oxygen analogues of the prostaglandin targets. 2014-08-13T14:26:29Z 2014-08-13T14:26:29Z 2006 Doctoral Thesis Doctoral PhD http://hdl.handle.net/11427/6312 eng application/pdf Department of Chemistry Faculty of Science University of Cape Town |
| spellingShingle | Chemistry Haupt, Hayley Claire Strategies towards the synthesis of prostaglandin analogues |
| thesis_degree_str | Doctoral |
| title | Strategies towards the synthesis of prostaglandin analogues |
| title_full | Strategies towards the synthesis of prostaglandin analogues |
| title_fullStr | Strategies towards the synthesis of prostaglandin analogues |
| title_full_unstemmed | Strategies towards the synthesis of prostaglandin analogues |
| title_short | Strategies towards the synthesis of prostaglandin analogues |
| title_sort | strategies towards the synthesis of prostaglandin analogues |
| topic | Chemistry |
| url | http://hdl.handle.net/11427/6312 |
| work_keys_str_mv | AT haupthayleyclaire strategiestowardsthesynthesisofprostaglandinanalogues |