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dc.contributor.authorLeisch, Hannes G.en_US
dc.date.accessioned2009-05-28T16:39:31Z
dc.date.available2009-05-28T16:39:31Z
dc.date.issued2009-05-28T16:39:31Z
dc.identifier.urihttp://hdl.handle.net/10464/1444
dc.description.abstractThe present thesis describes our latest results in the chemistry of morphine alkaloids. An enantiodivergent synthesis of codeine utilizing a cis-cyclohexadiene diol derived from microbial whole cell oxidation of ~-bromoethylbenzene,as starting material is discussed. The total synthesis of (+)-codeine in 14 steps featuring a Mitsunobu inversion and two intramolecular Heck cyclizations is presented. Investigation of a regioselective nucleophilic opening of a homochiral vinyl oxirane, which led to a total synthesis of the natural isomer of codeine, is detailed. Furthermore, described herein are novel methodologies designed for the transformation of naturally occurring opiates into medicinally relevant derivatives. Two studies on the conversion of thebaine into the commercially available analgesic hydrocodone, two novel ·transition metal catalyzed N-demethylation procedures for opioids, and the development of a catalytic protocol for N-demethylation and Nacylation of morphine and tropane alkaloids are presented. In addition, reactions of a menthol-based version of the Burgess reagent with epoxides are discussed. The synthetic utility of this novel chiral derivative of the Burgess reagent was demonstrated by an enantiodivergent formal total synthesis of balanol. iien_US
dc.language.isoengen_US
dc.publisherBrock Universityen_US
dc.subjectCodeine--Synthesis.en_US
dc.titleEnantiodivergent chemoenzymatic synthesis of codeineen_US
dc.typeElectronic Thesis or Dissertationen_US
dc.degree.namePh.D. Biotechnologyen_US
dc.degree.levelDoctoralen_US
dc.contributor.departmentCentre for Biotechnologyen_US
dc.degree.disciplineFaculty of Mathematics and Scienceen_US


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