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

 

Show simple item record

dc.contributor.advisor Hunter, Roger en_ZA
dc.contributor.advisor Nagorny, Pavel en_ZA
dc.contributor.author Bixa, Thobela Lukas en_ZA
dc.date.accessioned 2014-08-20T19:27:39Z
dc.date.available 2014-08-20T19:27:39Z
dc.date.issued 2013 en_ZA
dc.identifier.citation Bixa, 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.uri http://hdl.handle.net/11427/6637
dc.description.abstract 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. en_ZA
dc.language.iso eng en_ZA
dc.title The use of chiral auxiliaries in the synthesis of chemically and biologically important chiral compunds en_ZA
dc.type Master Thesis
uct.type.publication Research en_ZA
uct.type.resource Thesis en_ZA
dc.publisher.institution University of Cape Town
dc.publisher.faculty Faculty of Science en_ZA
dc.publisher.department Department of Chemistry en_ZA
dc.type.qualificationlevel Masters
dc.type.qualificationname MSc en_ZA
uct.type.filetype Text
uct.type.filetype Image
dc.identifier.apacitation Bixa, 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/11427/6637 en_ZA
dc.identifier.chicagocitation Bixa, 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/11427/6637 en_ZA
dc.identifier.vancouvercitation Bixa 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/11427/6637 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


Files in this item

This item appears in the following Collection(s)

Show simple item record