The University of Southampton
University of Southampton Institutional Repository

Synthesis of the pedamide fragment of onnamide F

Synthesis of the pedamide fragment of onnamide F
Synthesis of the pedamide fragment of onnamide F

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.

University of Southampton
Buffham, William John
22ca9777-958c-4963-9ad0-48691081025e
Buffham, William John
22ca9777-958c-4963-9ad0-48691081025e

Buffham, William John (2008) Synthesis of the pedamide fragment of onnamide F. University of Southampton, Doctoral Thesis.

Record type: Thesis (Doctoral)

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.

Text
1219651.pdf - Version of Record
Available under License University of Southampton Thesis Licence.
Download (12MB)

More information

Published date: 2008

Identifiers

Local EPrints ID: 466567
URI: http://eprints.soton.ac.uk/id/eprint/466567
PURE UUID: 8a5f4dd5-c286-4be5-93a0-1f78815ff935

Catalogue record

Date deposited: 05 Jul 2022 05:49
Last modified: 23 Jul 2022 02:20

Export record

Contributors

Author: William John Buffham

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of http://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×