In this thesis is presented work carried out during the course of the last 42
months. It concerns approaches towards total syntheses of the complanadine
alkaloids. The main focus is the development of a model system to establish the
viability of the key step in our proposed route to the complanadines. The thesis
is divided into five chapters.
Chapter 1 is an introduction to the complanadines, their biological activity and
accomplished total syntheses to date. A brief introduction to the Diels–Alder
reaction and selected examples of its application in the total syntheses of
natural products are given. The Kondrat’eva oxazole–olefin hetero-Diels–Alder
reaction as a method of pyridine formation is described and its application in the
total synthesis of natural products is reviewed.
Chapter 2 is the first part of the results and discussion section. It details our
retrosynthetic analysis of complanadine A, outlines the corresponding proposed
forward synthesis and presents a model system designed and synthesised to
test the applicability of the Kondrat’eva oxazole–olefin hetero-Diels–Alder
reaction in the context of our proposed total synthesis.
Chapter 3 discusses work carried out in approaches to the total synthesis of
complanadines and their monomeric subunit, lycodine, by means of the
methodology developed in the previous chapter.
Chapter 4 is the experimental section, which gives descriptions of the synthetic
procedures employed and spectroscopic data for all compounds synthesised,
both novel and previously reported, as discussed in Chapter 2 and Chapter 3.
Supplementary information such as X-Ray data for synthesised compounds and
selected NMR spectra are enclosed in the appendices.
|Date of Award
|27 Jul 2012
|Simon Lewis (Supervisor) & Jonathan Williams (Supervisor)