Towards onnamide F : a nematocide from the marine sponge Trachycladus laevispirulifer
Towards onnamide F : a nematocide from the marine sponge Trachycladus laevispirulifer
Onnamide F is a recently isolated natural product from the southern Australian marine sponge, Trachycladus laevispirulifer, that has shown significant antifungal and nematocidal activity.1 Onnamide F contains a tetrahydropyran substructure, known as pederic acid, and an amide bond linkage to a second tetrahydropyran. To date no total synthesis of onnamide F has been reported. A range of tetrahydropyrans with structural similarities to pederic acid were synthesised using a new Lewis acid mediated cyclisation reaction. Additionally, a diastereoselective route to tetrahydropyrans containing the exo-methylene functionality at C4 has been developed. A useful new route to the pederic acid precursor pederamide has been established. The tetrahydropyran skeleton was formed by a new Lewis aicd mediated cyclisation reaction between 3,4-Dimethylpent-4-en-2-ol and frYms-cinnamaldehyde, promoted by benzyltriethylammonium aluminium chloride. Further transformations gave us the opportunity to establish the correct oxidation level at the anomeric centre. Methyl ether formation followed by removal of the acetate group furnished a secondary alcohol which could be resolved via formation of the (+)-acetylmandelate ester. The enantiomerically pure tetrahydropyran was subjected to a Dess-Martin oxidation. Treatment with TMSCN followed by borax induced hydrolysis gave pederamide and its diastereoisomer.
University of Southampton
Rainbow, Simon C
6e4f7772-fecf-43c1-9621-2ff1bb9ad17a
2008
Rainbow, Simon C
6e4f7772-fecf-43c1-9621-2ff1bb9ad17a
Rainbow, Simon C
(2008)
Towards onnamide F : a nematocide from the marine sponge Trachycladus laevispirulifer.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
Onnamide F is a recently isolated natural product from the southern Australian marine sponge, Trachycladus laevispirulifer, that has shown significant antifungal and nematocidal activity.1 Onnamide F contains a tetrahydropyran substructure, known as pederic acid, and an amide bond linkage to a second tetrahydropyran. To date no total synthesis of onnamide F has been reported. A range of tetrahydropyrans with structural similarities to pederic acid were synthesised using a new Lewis acid mediated cyclisation reaction. Additionally, a diastereoselective route to tetrahydropyrans containing the exo-methylene functionality at C4 has been developed. A useful new route to the pederic acid precursor pederamide has been established. The tetrahydropyran skeleton was formed by a new Lewis aicd mediated cyclisation reaction between 3,4-Dimethylpent-4-en-2-ol and frYms-cinnamaldehyde, promoted by benzyltriethylammonium aluminium chloride. Further transformations gave us the opportunity to establish the correct oxidation level at the anomeric centre. Methyl ether formation followed by removal of the acetate group furnished a secondary alcohol which could be resolved via formation of the (+)-acetylmandelate ester. The enantiomerically pure tetrahydropyran was subjected to a Dess-Martin oxidation. Treatment with TMSCN followed by borax induced hydrolysis gave pederamide and its diastereoisomer.
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Published date: 2008
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Local EPrints ID: 466556
URI: http://eprints.soton.ac.uk/id/eprint/466556
PURE UUID: c7fb6e30-c03c-4dd1-a821-22cad20e0f52
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Date deposited: 05 Jul 2022 05:47
Last modified: 16 Mar 2024 20:46
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Author:
Simon C Rainbow
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