Studies directed towards the total synthesis of the natural product diazonamide A

Abstract

This dissertation is devoted to our synthetic studies aimed at the total synthesis of the natural product diazonamide A. Chapter 1 serves as an introduction to the diazonamides with a discussion of related marine cyclopeptides, previous synthetic work, and our retrosynthetic analysis. In Chapter 2, the development of a methodology for constructing benzofuran-2-ones related to the IHG-rings of diazonamide A using the Pummerer reaction is presented. Chapter 3 describes the preparation of bis-benzylic radicals and an examination of their chemical properties. A new methodology for the synthesis of 2,4-disubstituted oxazoles is reported in Chapter 4. Chapter 5 details the synthesis of several advanced model systems including the completion of the IHGCDEFrings. Finally, Chapter 6 contains a description of the experiments performed along with the relevant analytical data.