Oxidative Dearomatization / Diels-Alder Approaches to Maoecrystal V and the Gibberellin Family of Natural Products
AuthorSmith, Brandon Robert
AdvisorNjardarson, Jon T.
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 10-May-2019
AbstractSynthetic approaches to the complex natural product maoecrystal V and the gibberellin family of natural products are presented. The two approaches are united by an oxidative dearomatization / intramolecular Diels Alder strategy for the construction of [2.2.2]- bicyclooctenes. Chapter 1 highlights previous synthetic approaches for the synthesis of maoecrystal V and Chapter 2 chronicles my efforts toward a double-Diels-Alder approach toward maoecrystal V. In the course of investigating a hetero-Diels-Alder strategy for construction of maoecrystal V’s tetrahydrofuran ring several fragmentation and rearrangements of the [2.2.2]-bicyclooctene core were encountered. One of these, a novel skeletal rearrangement from [2.2.2] to [3.2.1]-bicyclooctene, was then utilized for entry into the gibberellin family of natural products. Chapter 3 discusses previous syntheses of gibberellins while Chapter 4 details my entry into this family of natural products and further exploration of the novel skeletal rearrangement. Chapter 5 discusses my contributions to the field of bicyclic and tricyclic guanidine synthesis. Finally, Chapter 6 highlights my work related to pharmaceutical drug analysis, focusing on less commonly utilized elemental substitutions.
Degree ProgramGraduate College