Show simple item record

dc.contributor.authorJin, Yunho
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.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.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

Files in this item


There are no files associated with this item.

This item appears in the following Collection(s)

Show simple item record