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.
Department
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