Synthesis of the pedamide fragment of onnamide F

Abstract

This thesis is concerned with the synthesis of two key fragments of onnamide F, a marine natural product isolated from the sponge Trachycladus laevispirulifer. Onnamide F has been shown to be a particularly potent inhibitor of fungal growth and the development of parasitic larvae. Onnamide F has not been synthesised previously, but synthetic approaches to the structurally related natural products pederin, mycalamides A and B, theopederin D, onnamide A and psymberin / irciniastatin A are discussed in Chapter 1. Chapter 2 details a racemic synthesis of the central tetrahydropyran fragment of onnamide F. The realisation of an asymmetric synthesis of the pedamide fragment based on the aforementioned synthesis is described in Chapter 3. Details of key ring- hydroxylation, expansion and cyclisation reactions are presented, including discussion of the influence of internal steric and kinetic factors on their stereochemical course. Optimisation of the key cyclisation reaction that delivers the required functionalised THP system proved challenging and required modification of the original synthetic target. This work, and synthesis of a key conjugated diene fragment are discussed in Chapter 4. Some initial research towards a formal synthesis of the related natural product psymberin is described in Chapter 5.

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