Studies directed towards the total synthesis of the natural product Taxol

Abstract

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.