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Title: Progress Toward the Total Synthesis of Paecilospirone
Authors: Landry, Matthew Leo
Advisors: Doyle, Abigail G.
Department: Chemistry
Class Year: 2013
Abstract: Progress towards the total synthesis of paecilospirone, a microtubule inhibiting natural product, is reported. The stereochemical outcome of the proposed steps has been verified by both a computational study and the synthesis of a model system. The synthesis incorporates the use of modern methods, including organocatalytic cyclization, palladium- and nickel-catalyzed crosscouplings, and oxidative spiroketalization. The use of these methods allows for the more modular, efficient, and sustainable synthesis of a potentially valuable antitumor compound. Additionally, the incorporation of novel methods in the synthesis of a complex target demonstrates the limitations and benefits of these modern transformations, and will serve to inform their use in future syntheses.
Extent: 186 pages
Access Restrictions: Walk-in Access. This thesis can only be viewed on computer terminals at the Mudd Manuscript Library.
Type of Material: Princeton University Senior Theses
Language: en_US
Appears in Collections:Chemistry, 1926-2020

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