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dc.contributor.authorVarghese, Vimal
dc.date.accessioned2015-01-15T16:16:42Z
dc.date.available2015-01-15T16:16:42Z
dc.date.issued2015-01-15
dc.identifier.urihttp://hdl.handle.net/10464/5980
dc.description.abstractThis thesis describes the chemoenzymatic synthesis of three morphine alkaloids. The total synthesis of dihydrocodeine and hydrocodone was accomplished starting from bromobenzene in 16 and 17 steps, respectively. The key steps included a microbial oxidation of bromobenzene by E. coli JM109 (pDTG601A), a Kazmaier-Claisen rearrangement of glycinate ester to generate C-9 and C-14 stereo centers, a Johnson-Claisen rearrangement to set the C-13 quaternary center, and a C-10/C-11 ring closure via a Friedel-Crafts reaction. In addition, the total synthesis of ent-hydromorphone starting from β-bromoethylbenzene in 12 steps is also described. The key reactions included the enzymatic dihydroxylation of β-bromoethylbenzene to the corresponding cis-cyclohexadienediol, a Mitsunobu reaction, and an oxidative dearomatization followed by an intramolecular [4+2] cycloaddition.en_US
dc.language.isoengen_US
dc.publisherBrock Universityen_US
dc.subjectTotal synthesisen_US
dc.subjectChemoenzymaticen_US
dc.subjectNatural producten_US
dc.subjectMorphine alkaloidsen_US
dc.titleChemoenzymatic Total Synthesis of Morphine alkaloids: Synthesis of Dihydrocodeine and Hydrocodone via a Double Claisen Strategy and ent-Hydromorphone via an Oxidative Dearomatization/intramolecular [4+2] Cycloadditionen_US
dc.typeElectronic Thesis or Dissertationen
dc.degree.namePh.D. Chemistryen_US
dc.degree.levelDoctoralen_US
dc.contributor.departmentDepartment of Chemistryen_US
dc.degree.disciplineFaculty of Mathematics and Scienceen_US
dc.embargo.termsNoneen_US
refterms.dateFOA2021-07-31T01:49:14Z


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