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Chemoenzymatic synthesis of amaryllidaceae alkaloids and their C-1 analogues : symmetry based approach to total synthesis of thebaine

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dc.contributor.author Collins, Jonathan A.
dc.date.accessioned 2010-10-26T18:45:33Z
dc.date.available 2010-10-26T18:45:33Z
dc.date.issued 2010-10-26
dc.identifier.uri http://hdl.handle.net/10464/3058
dc.description.abstract Described herein is the chemoenzymatic total synthesis of several Amaryllidaceae constituents and their unnatural C-I analogues. A new approach to pancratistatin and related compounds will be discussed along with the completed total synthesis of 7 -deoxypancratistatin and trans-dihydrolycoricidine. Evaluation of all new C-l analogues as cancer cell growth inhibitory agents is described. The enzymatic oxidation of dibromobenzenes by Escherichia coli 1M 109 (pDTG60 1) is presented along with conversion of their metabolites to (-)-conduritol E. Investigation into the steric and functional factors governing the enzymatic dihydroxylation of various benzoates by the same organism is also discussed. The synthetic utility of these metabolites is demonstrated through their conversion to pseudo-sugars, aminocyclitols, and complex bicyclic ring systems. The current work on the total synthesis of some morphine alkaloids is also presented. Highlighted will be the synthesis of several model systems related to the efficient total synthesis of thebaine. en_US
dc.language.iso eng en_US
dc.publisher Brock University en_US
dc.subject Alkaloids -- Synthesis en_US
dc.title Chemoenzymatic synthesis of amaryllidaceae alkaloids and their C-1 analogues : symmetry based approach to total synthesis of thebaine en_US
dc.type Electronic Thesis or Dissertation en_US
dc.degree.name Ph.D. Chemistry en_US
dc.degree.level Doctoral en_US
dc.contributor.department Department of Chemistry en_US
dc.degree.discipline Faculty of Mathematics and Science en_US


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