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dc.contributor.authorJin, Yunho
dc.date.accessioned2014-03-03T21:17:40Z
dc.date.available2014-03-03T21:17:40Z
dc.date.issued2004-05
dc.identifier.otherjin_yunho_200405_ms
dc.identifier.urihttp://purl.galileo.usg.edu/uga_etd/jin_yunho_200405_ms
dc.identifier.urihttp://hdl.handle.net/10724/21540
dc.description.abstractThe focus of this thesis is on the asymmetric synthesis of dioxolane and various novel carbocyclic nucleoside analogues with antiviral activity. Enantiomerically pure 5-alkyluracil-1,3-dioxolane nucleoside analogues were synthesized by palladium mediated cross-Stille coupling reaction from L-gulono-?-lactone in 17 steps. The synthetic methodology of enantiomerically pure key intermediates for carbocyclic nucleosides, D- and L-2-cyclopentenone, were developed by ring-closing metathesis reaction from D-ribose in 8 steps, which were utilized to synthesize D-cyclopetenyl and cyclopentyl nucleosides. Among them, D-cyclopetenyl adenine, cytosine and 5-F-cytosine analogues were found to be active against orthopox virus including smallpox, monkeypox, and cowpox virus. Enantiomerically pure D-2’-fluoro-2’,3’-dideoxy-2’,3’-didehydro and D-3’-fluoro-2’,3’- dideoxy-2’,3’-didehydro carbocyclic nucleosides were synthesized using epoxide ring opening reduction from D-ribose in 24 and 23 steps, respectively.
dc.languageeng
dc.publisheruga
dc.rightspublic
dc.subject1,3-Dioxolanyl Nucleoside
dc.subjectCarbocyclic Nucleoside
dc.subjectD and L-Cyclopentenone.
dc.titleSyntheses of 1,3-dioxolanyl and carbocyclic nucleosides as potential antiviral agnets [sic]
dc.typeThesis
dc.description.degreeMS
dc.description.departmentPharmacy (Medicinial Chemistry)
dc.description.majorPharmacy (Medicinial Chemistry)
dc.description.advisorChung. K. Chu
dc.description.committeeChung. K. Chu
dc.description.committeeA. C. Capomacchia
dc.description.committeeWarren Beach


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