Studies directed towards the total synthesis of the natural product Taxol
Allison, Jeffrey Corbin
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This dissertation is devoted to our synthetic work focused at the total synthesis of the natural product Taxol. Chapter 1 serves as an introduction to the Taxane family with a discussion on related anti-tumor agents, previous synthetic work, and our retrosynthetic analysis. Chapter 2 describes our approach to synthesizing a Taxol A-ring fragment using classical Diels-Alder chemistry. Chapter 3 details our implementation of a modified Birch reduction to afford a Taxol C-ring fragment. In Chapter 4, our exploration of [2,3] sigmatropic rearrangements with Taxane ether and thioether derivatives is presented. Chapter 5 examines our advances in the [2,3] rearrangements using Taxane amine derivatives. Finally, Chapter 6 contains a description of the experiments performed along with the relevant analytical data.