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dc.contributor.advisorChristie, Hamish S.en_US
dc.contributor.authorChang, Tsuhen Michelle
dc.creatorChang, Tsuhen Michelleen_US
dc.date.accessioned2012-06-11T22:17:48Z
dc.date.available2012-06-11T22:17:48Z
dc.date.issued2012
dc.identifier.urihttp://hdl.handle.net/10150/228493
dc.description.abstractStrategies to synthesize the natural product maoecrystal V have been investigated. The initial strategy involved a tandem Michael-aldol reaction to form the [2.2.2] bicyclic core of maoecrystal V. This proposed route was not successful. A modified route to maoecrystal V, inspired by studies on the aldol ring closure reactions, enabled the synthesis of a complex intermediate that allowed for the formation of the core structure. Further elaboration of this key intermediate afforded the methodology to form four of the five rings in maoecrystal V. Additionally, this key intermediate allowed for further modifications that can potentially be an entry point toward an enantioselective synthesis of maoecrystal V that intersects with the initial synthesis of the racemic compound.
dc.language.isoenen_US
dc.publisherThe University of Arizona.en_US
dc.rightsCopyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.en_US
dc.subjectChemistryen_US
dc.subjectMaoecrystal Ven_US
dc.subjectTotal Synthesisen_US
dc.titleProgress Toward the Total Synthesis of the Highly Selective Cytotoxic Natural Product, Maoecrystal Ven_US
dc.typetexten_US
dc.typeElectronic Dissertationen_US
thesis.degree.grantorUniversity of Arizonaen_US
thesis.degree.leveldoctoralen_US
dc.contributor.committeememberWalker, F. Annen_US
dc.contributor.committeememberJewett, Johnen_US
dc.contributor.committeememberChristie, Hamish S.en_US
dc.contributor.committeememberLichtenberger, Dennisen_US
dc.description.releaseRelease after 18-Oct-2012en_US
thesis.degree.disciplineGraduate Collegeen_US
thesis.degree.disciplineChemistryen_US
thesis.degree.namePh.D.en_US
refterms.dateFOA2012-10-18T00:00:00Z
html.description.abstractStrategies to synthesize the natural product maoecrystal V have been investigated. The initial strategy involved a tandem Michael-aldol reaction to form the [2.2.2] bicyclic core of maoecrystal V. This proposed route was not successful. A modified route to maoecrystal V, inspired by studies on the aldol ring closure reactions, enabled the synthesis of a complex intermediate that allowed for the formation of the core structure. Further elaboration of this key intermediate afforded the methodology to form four of the five rings in maoecrystal V. Additionally, this key intermediate allowed for further modifications that can potentially be an entry point toward an enantioselective synthesis of maoecrystal V that intersects with the initial synthesis of the racemic compound.


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