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Radical cyclisation studies of chiral α-acylamino radicals : a model study towards Tacaman indole alkaloid synthesis
Includes bibliographical references.
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| Main Author: | |
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| Other Authors: | |
| Format: | Thesis |
| Language: | English |
| Published: |
Department of Chemistry
2016
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| _version_ | 1867613171843334145 |
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| access_status_str | Open Access |
| author | Clauss, Rainer |
| author2 | Hunter, Roger |
| author_browse | Clauss, Rainer Hunter, Roger |
| author_facet | Hunter, Roger Clauss, Rainer |
| author_sort | Clauss, Rainer |
| collection | Thesis |
| description | Includes bibliographical references. |
| format | Thesis |
| id | oai:open.uct.ac.za:11427/16138 |
| institution | University of Cape Town (South Africa) |
| language | eng |
| last_indexed | 2026-06-10T12:31:54.917Z |
| license_str | Not specified — see source repository |
| provenance_str_mv | Harvested via OAI-PMH from UCTD — University of Cape Town Open Access Repository |
| publishDate | 2016 |
| publishDateRange | 2016 |
| publishDateSort | 2016 |
| 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:11427/16138 Radical cyclisation studies of chiral α-acylamino radicals : a model study towards Tacaman indole alkaloid synthesis Clauss, Rainer Hunter, Roger Chemistry Includes bibliographical references. he radical cyclisation of chiral 4,5-substituted N-acyl-2-aza-6-heptenyl radicals, derived from D-ribose, has been undertaken as a model stuay towards Tacaman indole alkaloid synthesis. The radical cyclisations were conducted using tributyltin hydride/AIBN in refluxing benzene. The α-acylamino radicals added to double bonds which were activated by an ethoxycarbonyl substituent. No reduction of the radicals by the tributyltin hydride was observed. Those radicals incorporating an isopropylidene ketal at the 4 and 5 positions as chiral auxiliary showed excellent regio- and stereoselectivity. Out of a possible 4 diastereomers, only two were obtained in a 2:8 ratio. It was established that the isopropylidene ketal directed the cyclisation stereoselectively and that no stereoselectivity was observed in the absence of the chiral auxiliary. 2016-01-02T04:52:10Z 2016-01-02T04:52:10Z 1996 Master Thesis Masters MSc http://hdl.handle.net/11427/16138 eng application/pdf Department of Chemistry Faculty of Science University of Cape Town |
| spellingShingle | Chemistry Clauss, Rainer Radical cyclisation studies of chiral α-acylamino radicals : a model study towards Tacaman indole alkaloid synthesis |
| thesis_degree_str | Master's |
| title | Radical cyclisation studies of chiral α-acylamino radicals : a model study towards Tacaman indole alkaloid synthesis |
| title_full | Radical cyclisation studies of chiral α-acylamino radicals : a model study towards Tacaman indole alkaloid synthesis |
| title_fullStr | Radical cyclisation studies of chiral α-acylamino radicals : a model study towards Tacaman indole alkaloid synthesis |
| title_full_unstemmed | Radical cyclisation studies of chiral α-acylamino radicals : a model study towards Tacaman indole alkaloid synthesis |
| title_short | Radical cyclisation studies of chiral α-acylamino radicals : a model study towards Tacaman indole alkaloid synthesis |
| title_sort | radical cyclisation studies of chiral α acylamino radicals a model study towards tacaman indole alkaloid synthesis |
| topic | Chemistry |
| url | http://hdl.handle.net/11427/16138 |
| work_keys_str_mv | AT claussrainer radicalcyclisationstudiesofchiralaacylaminoradicalsamodelstudytowardstacamanindolealkaloidsynthesis |