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Towards the total synthesis of Chrysophaentin F

Towards the total synthesis of Chrysophaentin F
Towards the total synthesis of Chrysophaentin F
This thesis describes the synthetic work towards the natural product Chrysophaentin F which has been extracted from the alga Chrysophaeum taylori. This bisdiarylbutene macrocycle exhibits antimicrobial properties against gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococcus faecium (VREF) (MIC50 (MRSA) = 4.2 ± 1.3 ?g/mL).

Investigation of the key steps on an unchlorinated analogue allowed us to determine what strategy would be best to access the natural product. The formation of the desired core structure relied on a Chan-Lam-Evans coupling reaction, a Pd catalysed coupling reaction and a RCAM reaction to create the pivotal bonds of the complex scaffold. The investigation on a model system to form the vinyl chloride bridge has also been performed bringing insight on the possible regioselectivity of the necessary late stage hydrochlorination reaction.

Finally the synthesis towards the chlorinated macrocycle was started and advanced enough to access some key intermediates which despite some unforeseen difficulties proved that the natural product is now at reach following the strategy developed for the unchlorinated analogue.
Vendeville, Jean-Baptiste
9f2c6155-cf23-4733-9402-33633fb5bb47
Vendeville, Jean-Baptiste
9f2c6155-cf23-4733-9402-33633fb5bb47
Harrowven, David
bddcfab6-dbde-49df-aec2-42abbcf5d10b

Vendeville, Jean-Baptiste (2014) Towards the total synthesis of Chrysophaentin F. University of Southampton, Department of Chemistry, Doctoral Thesis, 379pp.

Record type: Thesis (Doctoral)

Abstract

This thesis describes the synthetic work towards the natural product Chrysophaentin F which has been extracted from the alga Chrysophaeum taylori. This bisdiarylbutene macrocycle exhibits antimicrobial properties against gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococcus faecium (VREF) (MIC50 (MRSA) = 4.2 ± 1.3 ?g/mL).

Investigation of the key steps on an unchlorinated analogue allowed us to determine what strategy would be best to access the natural product. The formation of the desired core structure relied on a Chan-Lam-Evans coupling reaction, a Pd catalysed coupling reaction and a RCAM reaction to create the pivotal bonds of the complex scaffold. The investigation on a model system to form the vinyl chloride bridge has also been performed bringing insight on the possible regioselectivity of the necessary late stage hydrochlorination reaction.

Finally the synthesis towards the chlorinated macrocycle was started and advanced enough to access some key intermediates which despite some unforeseen difficulties proved that the natural product is now at reach following the strategy developed for the unchlorinated analogue.

Text
JB Vendeville_final version Ph D .pdf - Other
Restricted to Repository staff only until 31 May 2020.

More information

Published date: 1 November 2014
Organisations: University of Southampton, Chemistry

Identifiers

Local EPrints ID: 377599
URI: http://eprints.soton.ac.uk/id/eprint/377599
PURE UUID: cd5b7636-1a71-4b98-a64a-ef21003f7313
ORCID for David Harrowven: ORCID iD orcid.org/0000-0001-6730-3573

Catalogue record

Date deposited: 10 Jun 2015 14:04
Last modified: 22 May 2019 00:37

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Contributors

Author: Jean-Baptiste Vendeville
Thesis advisor: David Harrowven ORCID iD

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