Date of Award

Spring 1-1-2011

Document Type

Dissertation

Degree Name

Doctor of Philosophy (PhD)

Department

Chemistry & Biochemistry

First Advisor

Tarek Sammakia

Second Advisor

Xiang Wang

Third Advisor

Andrew Phillips

Abstract

This dissertation describes efforts toward the total synthesis of diazonamide A, a complex marine natural product. First, efficient methods to prepare 3,3-diaryloxindoles from 3-aryloxindoles were developed via either Pd-catalyzed alpha-arylations or nucleophilic aromatic substitutions using the oxindole enolate as the nucleophile. Second, this method has been successfully applied to a formal synthesis of diazonamide A via the highly diastereoselective construction of the C10 quaternary center. Third, a cyclization precursor for a cascade alpha-arylation/direct arylation approach to the total synthesis was synthesized and tested, and this substrate was found to be failed to cyclize. Finally, two approaches to the synthesis of the aromatic core of diazonamide A, via our Pd-catalyzed alpha-arylation method and Au-catalyzed oxazole formation developed by Liming Zhang and coworkers, were attempted. Unfortunately, neither of these two methods was able to provide the desired product.

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