Progress Toward the Total Synthesis of the Highly Selective Cytotoxic Natural Product, Maoecrystal V
AuthorChang, Tsuhen Michelle
AdvisorChristie, Hamish S.
MetadataShow full item record
PublisherThe University of Arizona.
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.
EmbargoRelease after 18-Oct-2012
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.
Degree ProgramGraduate College