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dc.contributor.authorMurphy, Brennan
dc.date.accessioned2015-08-21T13:37:57Z
dc.date.available2015-08-21T13:37:57Z
dc.identifier.urihttp://hdl.handle.net/10464/7050
dc.description.abstractTwo synthetic projects were embarked upon, both fraught with protecting group nuance and reaction selectivity. Transformations of the opiate skeleton remain a valuable tool for the development of new medicines. Thebaine, a biosynthetic intermediate in the expression of morphine, was converted in three steps to oripavine through two parallel modes. Through the use of protecting group manipulations, two irreversible scaffold rearrangements were avoided during aryl methyl ether bond cleavage. This chemistry constitutes a new path in manipulations of the morphinan scaffold through protective groups. A new compound family, the flacourtosides, contains an unusual cyclohexenone fragment. The newly described compounds show in preliminary tests antiviral activity against dengue and chikungunya. This aglycone was approached on three pathways, all beginning with the chemoenzymatic dihydroxylation of benzoic acid. A first attempt from a known vinyl epoxide failed to epimerize and cooperate under deprotective conditions. A second and third attempt made use of a diastereoselective dihydroxylation reaction, which was critical in reaching the correct stereochemistry and oxidation state. The methyl ester of the aglycone was prepared, constituting the first synthesis of the non-trivial natural product framework.en_US
dc.language.isoengen_US
dc.publisherBrock Universityen_US
dc.subjectthebaineen_US
dc.subjectoripavineen_US
dc.subjectflacourtosideen_US
dc.subjectchemoenzymatic dihydroxylationen_US
dc.title3-O-Demethylation of thebaine and the synthesis of a flacourtia aglycone from benzoic acid.en_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


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