Progress Toward the Total Synthesis of the Highly Selective Cytotoxic Natural Product, Maoecrystal V

Persistent Link:
http://hdl.handle.net/10150/228493
Title:
Progress Toward the Total Synthesis of the Highly Selective Cytotoxic Natural Product, Maoecrystal V
Author:
Chang, Tsuhen Michelle
Issue Date:
2012
Publisher:
The University of Arizona.
Rights:
Copyright © 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.
Embargo:
Release after 18-Oct-2012
Abstract:
Strategies 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.
Type:
text; Electronic Dissertation
Keywords:
Chemistry; Maoecrystal V; Total Synthesis
Degree Name:
Ph.D.
Degree Level:
doctoral
Degree Program:
Graduate College; Chemistry
Degree Grantor:
University of Arizona
Advisor:
Christie, Hamish S.

Full metadata record

DC FieldValue Language
dc.language.isoenen_US
dc.titleProgress Toward the Total Synthesis of the Highly Selective Cytotoxic Natural Product, Maoecrystal Ven_US
dc.creatorChang, Tsuhen Michelleen_US
dc.contributor.authorChang, Tsuhen Michelleen_US
dc.date.issued2012-
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.description.releaseRelease after 18-Oct-2012en_US
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.en_US
dc.typetexten_US
dc.typeElectronic Dissertationen_US
dc.subjectChemistryen_US
dc.subjectMaoecrystal Ven_US
dc.subjectTotal Synthesisen_US
thesis.degree.namePh.D.en_US
thesis.degree.leveldoctoralen_US
thesis.degree.disciplineGraduate Collegeen_US
thesis.degree.disciplineChemistryen_US
thesis.degree.grantorUniversity of Arizonaen_US
dc.contributor.advisorChristie, Hamish S.en_US
dc.contributor.committeememberWalker, F. Annen_US
dc.contributor.committeememberJewett, Johnen_US
dc.contributor.committeememberChristie, Hamish S.en_US
dc.contributor.committeememberLichtenberger, Dennisen_US
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