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dc.contributor.advisorKrische, Michael J.en
dc.creatorJones, Regan Andrewen
dc.date.accessioned2009-09-03T21:02:55Zen
dc.date.available2009-09-03T21:02:55Zen
dc.date.issued2009-05en
dc.identifier.urihttp://hdl.handle.net/2152/ETD-UT-2009-05-16en
dc.descriptiontexten
dc.description.abstractThe iridoids are a large family of monoterpenoid natural products that possess a wide range of biological activities. A great deal of research has already been done in the field of iridoid total synthesis, but limitations still remain. Specifically, few syntheses of iridoid β-glycosides have been reported. This work describes the 14 step asymmetric total synthesis of the iridoid β-glycoside (+)-geniposide utilizing a phosphine-catalyzed [3+2] cycloaddition as the key step. Other noteworthy steps in the synthesis include a palladium-catalyzed kinetic resolution and a previously unutilized method for iridoid glycosidation. In addition to describing the synthesis of (+)-geniposide, this dissertation will also review 1) phosphine-catalyzed cycloaddition reactions and 2) previous enantioselective total syntheses of iridoid glycosides.en
dc.format.mimetypeapplication/pdfen
dc.language.isoengen
dc.subjectPhosphine, Catalysis, [3+2] Cycloaddition, Synthesis, Iridoidsen
dc.titleThe asymmetric total synthesis of (+)-geniposide via phosphine-catalyzed [3+2] cycloadditionen
dc.contributor.committeeMemberMagnus, Philip D.en
dc.contributor.committeeMemberLiu, Hung-wenen
dc.contributor.committeeMemberMartin, Stephen F.en
dc.contributor.committeeMemberKerwin, Seanen
dc.description.departmentChemistry and Biochemistryen
dc.type.genreThesisen
thesis.degree.departmentChemistry and Biochemistryen
thesis.degree.disciplineChemistry and Biochemistryen
thesis.degree.grantorThe University of Texas at Austinen
thesis.degree.levelDoctoralen
thesis.degree.nameDoctor of Philosophyen


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