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dc.contributor.authorHurem, David
dc.date.accessioned2014-09-11T15:15:35Z
dc.date.available2014-09-11T15:15:35Z
dc.date.issued2014-09-11
dc.identifier.urihttp://hdl.handle.net/10464/5713
dc.description.abstractThe unnatural threo-6-acetoxy-5-hexadecanolide and the natural mosquito oviposition pheromone erythro-6-acetoxy-5-hexadecanolide were synthesized in a diastereodivergent fashion in 44% and 33% overall yield respectively from 5-bromovaleric acid and undecanal. The key step utilized a chemoenzymatic epoxidation-lactonization of a naturally available fatty acid to form the 6-hydroxy-5-hexadecanolide core.17 The epoxidation strategy was later adapted to allow for an asymmetric synthesis. Shi epoxidation afforded highly enantioenriched (5R, 6R)-6-hydroxyhexadecanolide (er = 10) in 70 % overall yield. Other derivatives of the chiral ketone catalyst were also screened. Finally, attempts were made to obtain the correct stereochemistry at C(6) of the target with a dynamic kinetic transformation using lipase and a transfer hydrogenation catalyst. Epimerization of the lactol with the transfer hydrogenation catalyst was successful, but lipase mediated reactions halted at <10 % conversion.en_US
dc.language.isoengen_US
dc.publisherBrock Universityen_US
dc.subjectNatural Product Synthesisen_US
dc.subjectGreen Chemistryen_US
dc.subjectAsymmetric Epoxidationen_US
dc.subjectChemoenzymatic Epoxidationen_US
dc.subjectInsect Pheromoneen_US
dc.titleRacemic and Enantioselective Total Syntheses of Mosquito Oviposition Pheromone from a Naturally Available Unsaturated Fatty Aciden_US
dc.typeElectronic Thesis or Dissertationen_US
dc.degree.nameM.Sc. Chemistryen_US
dc.degree.levelMastersen_US
dc.contributor.departmentDepartment of Chemistryen_US
dc.degree.disciplineFaculty of Mathematics and Scienceen_US
dc.embargo.termsNoneen_US


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