Silver-Mediated Trifluoromethoxylation of Aryl Nucleophiles and Synthesis of 3-Deoxy-3-Fluoromorphine

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Silver-Mediated Trifluoromethoxylation of Aryl Nucleophiles and Synthesis of 3-Deoxy-3-Fluoromorphine

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dc.contributor.advisor Ritter, Tobias
dc.contributor.author Liang, Theresa
dc.date.accessioned 2012-11-14T14:19:09Z
dc.date.issued 2012-11-14
dc.date.submitted 2012
dc.identifier.other http://dissertations.umi.com/gsas.harvard:10547 en
dc.identifier.uri http://nrs.harvard.edu/urn-3:HUL.InstRepos:9904007
dc.description.abstract Fluorine incorporation has become increasingly important in pharmaceutical applications. Upon fluorination and incorporation of fluorinated moieties such as trifluoromethoxy groups, many small molecules become more bioavailable and metabolically stable and additionally can better cross the blood-brain-barrier. This thesis describes the development of a method mediated by silver salts for the synthesis of pharmaceutical-like trifluoromethoxylated compounds via \(C-OCF_3\) bond formation. Additionally the synthesis of 3-deoxy-3-fluoromorphine via late-stage fluorination of morphine is described as well as in vitro and in vivo evaluation of 3-deoxy-3-fluoromorphine as a potential analgesic. en_US
dc.description.sponsorship Chemistry and Chemical Biology en_US
dc.language.iso en_US en_US
dash.license LAA
dc.subject antinociception en_US
dc.subject aryl trifluoromethyl ethers en_US
dc.subject cross-coupling en_US
dc.subject fluorinated morphine en_US
dc.subject silver-mediated en_US
dc.subject trifluoromethoxylation en_US
dc.subject chemistry en_US
dc.title Silver-Mediated Trifluoromethoxylation of Aryl Nucleophiles and Synthesis of 3-Deoxy-3-Fluoromorphine en_US
dc.type Thesis or Dissertation en_US
dash.depositing.author Liang, Theresa
dc.date.available 2012-11-14T14:19:09Z
thesis.degree.date 2012 en_US
thesis.degree.discipline Chemistry en_US
thesis.degree.grantor Harvard University en_US
thesis.degree.level doctoral en_US
thesis.degree.name Ph.D. en_US
dc.contributor.committeeMember Jacobsen, Eric en_US
dc.contributor.committeeMember Betley, Theodore en_US

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