Radical cyclisation studies of chiral α-acylamino radicals : a model study towards Tacaman indole alkaloid synthesis

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dc.contributor.advisorHunter, Rogeren_ZA
dc.contributor.authorClauss, Raineren_ZA
dc.date.accessioned2016-01-02T04:52:10Z
dc.date.available2016-01-02T04:52:10Z
dc.date.issued1996en_ZA
dc.descriptionIncludes bibliographical references.en_ZA
dc.description.abstracthe 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.en_ZA
dc.identifier.apacitationClauss, R. (1996). <i>Radical cyclisation studies of chiral α-acylamino radicals : a model study towards Tacaman indole alkaloid synthesis</i>. (Thesis). University of Cape Town ,Faculty of Science ,Department of Chemistry. Retrieved from http://hdl.handle.net/11427/16138en_ZA
dc.identifier.chicagocitationClauss, Rainer. <i>"Radical cyclisation studies of chiral α-acylamino radicals : a model study towards Tacaman indole alkaloid synthesis."</i> Thesis., University of Cape Town ,Faculty of Science ,Department of Chemistry, 1996. http://hdl.handle.net/11427/16138en_ZA
dc.identifier.citationClauss, R. 1996. Radical cyclisation studies of chiral α-acylamino radicals : a model study towards Tacaman indole alkaloid synthesis. University of Cape Town.en_ZA
dc.identifier.ris TY - Thesis / Dissertation AU - Clauss, Rainer AB - 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. DA - 1996 DB - OpenUCT DP - University of Cape Town LK - https://open.uct.ac.za PB - University of Cape Town PY - 1996 T1 - Radical cyclisation studies of chiral α-acylamino radicals : a model study towards Tacaman indole alkaloid synthesis TI - Radical cyclisation studies of chiral α-acylamino radicals : a model study towards Tacaman indole alkaloid synthesis UR - http://hdl.handle.net/11427/16138 ER - en_ZA
dc.identifier.urihttp://hdl.handle.net/11427/16138
dc.identifier.vancouvercitationClauss R. Radical cyclisation studies of chiral α-acylamino radicals : a model study towards Tacaman indole alkaloid synthesis. [Thesis]. University of Cape Town ,Faculty of Science ,Department of Chemistry, 1996 [cited yyyy month dd]. Available from: http://hdl.handle.net/11427/16138en_ZA
dc.language.isoengen_ZA
dc.publisher.departmentDepartment of Chemistryen_ZA
dc.publisher.facultyFaculty of Scienceen_ZA
dc.publisher.institutionUniversity of Cape Town
dc.subject.otherChemistryen_ZA
dc.titleRadical cyclisation studies of chiral α-acylamino radicals : a model study towards Tacaman indole alkaloid synthesisen_ZA
dc.typeMaster Thesis
dc.type.qualificationlevelMasters
dc.type.qualificationnameMScen_ZA
uct.type.filetypeText
uct.type.filetypeImage
uct.type.publicationResearchen_ZA
uct.type.resourceThesisen_ZA
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