The use of chiral auxiliaries in the synthesis of chemically and biologically important chiral compunds

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dc.contributor.advisorHunter, Rogeren_ZA
dc.contributor.advisorNagorny, Pavelen_ZA
dc.contributor.authorBixa, Thobela Lukasen_ZA
dc.date.accessioned2014-08-20T19:27:39Z
dc.date.available2014-08-20T19:27:39Z
dc.date.issued2013en_ZA
dc.description.abstractChiral synthons of chemical and biological importance have been synthesised using imidazolidinone and Evans' oxazolidinone chiral auxiliaries (CA). The thesis comprises two parts, which were carried out at the Universities of Cape Town, RSA and University of Michigan in the USA. In part 1, carried out in the Chemistry Department of the University of Cape Town, an imidazolidinone-CA was utilised in developing a malonate-based methodology to synthesise compounds containing a quaternary stereogenic centre (QSC). With this methodology, a small library of malonate-based QSC-containing synthons has been synthesised in both high yields (> 87 %) and high stereoselectivities (dr, ≥ 93 : 7 %). The CA was cleaved using an EtSLi SNAc reaction followed by a double reduction using the Fukuyama protocol followed by NaBH4 to afford α,α'-disubstituted-2-hydroxy synthons in 55-65% yield over two steps respectively. In part 2, carried out in the Chemistry Department at the University of Michigan, the macrolide core (10) of lactimidomycin was synthesised for biological evaluation over 11-linear steps in a 6.1 % overall yield. The synthesis exploited an Evans' oxazolidinonemediated aldol reaction to construct the Evans syn-adduct, a Suzuki cross-coupling for the (E,Z)-diene construction, and an intramolecular Horner-Wadsworth-Emmons olefination for construction of the E-enone of the macrolide.en_ZA
dc.identifier.apacitationBixa, T. L. (2013). <i>The use of chiral auxiliaries in the synthesis of chemically and biologically important chiral compunds</i>. (Thesis). University of Cape Town ,Faculty of Science ,Department of Chemistry. Retrieved from http://hdl.handle.net/11427/6637en_ZA
dc.identifier.chicagocitationBixa, Thobela Lukas. <i>"The use of chiral auxiliaries in the synthesis of chemically and biologically important chiral compunds."</i> Thesis., University of Cape Town ,Faculty of Science ,Department of Chemistry, 2013. http://hdl.handle.net/11427/6637en_ZA
dc.identifier.citationBixa, T. 2013. The use of chiral auxiliaries in the synthesis of chemically and biologically important chiral compunds. University of Cape Town.en_ZA
dc.identifier.ris TY - Thesis / Dissertation AU - Bixa, Thobela Lukas AB - Chiral synthons of chemical and biological importance have been synthesised using imidazolidinone and Evans' oxazolidinone chiral auxiliaries (CA). The thesis comprises two parts, which were carried out at the Universities of Cape Town, RSA and University of Michigan in the USA. In part 1, carried out in the Chemistry Department of the University of Cape Town, an imidazolidinone-CA was utilised in developing a malonate-based methodology to synthesise compounds containing a quaternary stereogenic centre (QSC). With this methodology, a small library of malonate-based QSC-containing synthons has been synthesised in both high yields (> 87 %) and high stereoselectivities (dr, ≥ 93 : 7 %). The CA was cleaved using an EtSLi SNAc reaction followed by a double reduction using the Fukuyama protocol followed by NaBH4 to afford α,α'-disubstituted-2-hydroxy synthons in 55-65% yield over two steps respectively. In part 2, carried out in the Chemistry Department at the University of Michigan, the macrolide core (10) of lactimidomycin was synthesised for biological evaluation over 11-linear steps in a 6.1 % overall yield. The synthesis exploited an Evans' oxazolidinonemediated aldol reaction to construct the Evans syn-adduct, a Suzuki cross-coupling for the (E,Z)-diene construction, and an intramolecular Horner-Wadsworth-Emmons olefination for construction of the E-enone of the macrolide. DA - 2013 DB - OpenUCT DP - University of Cape Town LK - https://open.uct.ac.za PB - University of Cape Town PY - 2013 T1 - The use of chiral auxiliaries in the synthesis of chemically and biologically important chiral compunds TI - The use of chiral auxiliaries in the synthesis of chemically and biologically important chiral compunds UR - http://hdl.handle.net/11427/6637 ER - en_ZA
dc.identifier.urihttp://hdl.handle.net/11427/6637
dc.identifier.vancouvercitationBixa TL. The use of chiral auxiliaries in the synthesis of chemically and biologically important chiral compunds. [Thesis]. University of Cape Town ,Faculty of Science ,Department of Chemistry, 2013 [cited yyyy month dd]. Available from: http://hdl.handle.net/11427/6637en_ZA
dc.language.isoengen_ZA
dc.publisher.departmentDepartment of Chemistryen_ZA
dc.publisher.facultyFaculty of Scienceen_ZA
dc.publisher.institutionUniversity of Cape Town
dc.titleThe use of chiral auxiliaries in the synthesis of chemically and biologically important chiral compundsen_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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