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Enantiodivergent chemoenzymatic synthesis of codeine

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dc.contributor.author Leisch, Hannes G. en_US
dc.date.accessioned 2009-05-28T16:39:31Z
dc.date.available 2009-05-28T16:39:31Z
dc.date.issued 2009-05-28T16:39:31Z
dc.identifier.uri http://hdl.handle.net/10464/1444
dc.description.abstract The 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. ii en_US
dc.language.iso eng en_US
dc.publisher Brock University en_US
dc.subject Codeine--Synthesis. en_US
dc.title Enantiodivergent chemoenzymatic synthesis of codeine en_US
dc.type Electronic Thesis or Dissertation en_US
dc.degree.name Ph.D. Biotechnology en_US
dc.degree.level Doctoral en_US
dc.contributor.department Centre for Biotechnology en_US
dc.degree.discipline Faculty of Mathematics and Science en_US


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