The asymmetric total synthesis of (+)-geniposide via phosphine-catalyzed [3+2] cycloaddition

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The asymmetric total synthesis of (+)-geniposide via phosphine-catalyzed [3+2] cycloaddition

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dc.contributor.advisor Krische, Michael J.
dc.creator Jones, Regan Andrew
dc.date.accessioned 2009-09-03T21:02:55Z
dc.date.available 2009-09-03T21:02:55Z
dc.date.created 2009-05
dc.date.issued 2009-09-03T21:02:55Z
dc.identifier.uri http://hdl.handle.net/2152/ETD-UT-2009-05-16
dc.description.abstract The 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.
dc.format.mimetype application/pdf
dc.language.iso eng
dc.subject Phosphine, Catalysis, [3+2] Cycloaddition, Synthesis, Iridoids
dc.title The asymmetric total synthesis of (+)-geniposide via phosphine-catalyzed [3+2] cycloaddition
dc.contributor.committeeMember Magnus, Philip D.
dc.contributor.committeeMember Liu, Hung-wen
dc.contributor.committeeMember Martin, Stephen F.
dc.contributor.committeeMember Kerwin, Sean
dc.description.department Chemistry and Biochemistry
dc.type.genre Thesis
dc.type.material text
thesis.degree.department Chemistry and Biochemistry
thesis.degree.discipline Chemistry and Biochemistry
thesis.degree.grantor The University of Texas at Austin
thesis.degree.level Doctoral
thesis.degree.name Doctor of Philosophy

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