The total synthesis of (±)-renieramycin g and studies toward the synthesis of (±)-lemonomycin and (±)-saframycin b

dc.contributor.advisorMagnus, Philip D.en
dc.creatorMatthews, Kenneth Stanleyen
dc.date.accessioned2008-08-28T22:27:02Zen
dc.date.available2008-08-28T22:27:02Zen
dc.date.issued2005en
dc.description.abstractHerein is described our synthetic approach to the tetrahydroisoquinoline alkaloids. The first chapter describes relevant background related to the biological significance of these alkaloids. The analysis of various syntheses of saframycins, renieramycins, and lemonomycin is also discussed. Chapter 2 describes the development of a new synthesis of 1,3-cis-substituted tetrahydroisoquinolines and a novel lactam formation in our approach to (±)-saframycin B. Chapter 3 applies the new tetrahydroisoquinoline formation toward the synthesis of (±)-lemonomycin. The bicyclo[3.2.1] system is constructed from an intramolecular N-acyliminium cyclization and leads to the synthesis (±)-lemonomycinone amide. Chapter 4 reports the total synthesis of (±)-renieramycin G from an advanced intermediate used in our approach to (±)-lemonomycin, demonstrating a divergent approach to the tetrahydroisoquinoline alkaloids. Chapter 5 contains the experimental details and characterization data for all new reported compounds.
dc.description.departmentChemistry and Biochemistryen
dc.description.departmentChemistryen
dc.format.mediumelectronicen
dc.identifierb60789670en
dc.identifier.oclc68225902en
dc.identifier.urihttp://hdl.handle.net/2152/1996en
dc.language.isoengen
dc.rightsCopyright is held by the author. Presentation of this material on the Libraries' web site by University Libraries, The University of Texas at Austin was made possible under a limited license grant from the author who has retained all copyrights in the works.en
dc.subject.lcshAlkaloidsen
dc.subject.lcshTetrahydroisoquinolinesen
dc.titleThe total synthesis of (±)-renieramycin g and studies toward the synthesis of (±)-lemonomycin and (±)-saframycin ben
dc.type.genreThesisen
thesis.degree.departmentChemistryen
thesis.degree.disciplineChemistryen
thesis.degree.grantorThe University of Texas at Austinen
thesis.degree.levelDoctoralen
thesis.degree.nameDoctor of Philosophyen

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