Development of methodologies employing rhodium catalysis and studies toward the total synthesis of cortistatin A

dc.contributor.advisorMartin, Stephen F.en
dc.contributor.committeeMemberBielawski, Christopheren
dc.contributor.committeeMemberLaude, Daviden
dc.contributor.committeeMemberKerwin, Seanen
dc.contributor.committeeMemberSessler, Jonathanen
dc.creatorSmith, Anna Jane, Ph. D.en
dc.date.accessioned2010-08-23T17:50:37Zen
dc.date.available2010-08-23T17:50:37Zen
dc.date.available2010-08-23T17:50:55Zen
dc.date.issued2009-12en
dc.date.submittedDecember 2009en
dc.date.updated2010-08-23T17:50:55Zen
dc.descriptiontexten
dc.description.abstract[Rh(CO]2Cl]2 has been shown to catalyze sequential, mechanistically- distinct transformations in one pot. Tandem allylic alkylation/cycloisomerization sequences have been developed to access valuable, complex structures from relatively simple substrates. A methodology for the enantioselective conjugate addition of 2-heteroaryl nucleophiles to a variety of Michael acceptors has been developed. This method was used successfully in an ongoing approach to the synthesis of cortistatin A. 10 linear steps have been completed towards the synthesis of cortistatin A, including a highly regioselective propargylation to install a quaternary carbon and a diastereoselective intramolecular Diels-Alder reaction.en
dc.description.departmentChemistry and Biochemistry
dc.format.mimetypeapplication/pdfen
dc.identifier.urihttp://hdl.handle.net/2152/ETD-UT-2009-12-653en
dc.language.isoengen
dc.subjectCortistatin Aen
dc.subjectTandem catalysisen
dc.subjectEnantioselective conjugate additionen
dc.titleDevelopment of methodologies employing rhodium catalysis and studies toward the total synthesis of cortistatin Aen
dc.type.genrethesisen
thesis.degree.departmentChemistry and Biochemistryen
thesis.degree.disciplineChemistryen
thesis.degree.grantorThe University of Texas at Austinen
thesis.degree.levelDoctoralen
thesis.degree.nameDoctor of Philosophyen

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