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Title: Towards onnamide F : a nematocide from the marine sponge Trachycladus laevispirulifer
Author: Rainbow, Simon C.
ISNI:       0000 0001 3505 5691
Awarding Body: University of Southampton
Current Institution: University of Southampton
Date of Award: 2008
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Onnamide F is a recently isolated natural product from the southern Australian marine sponge, Trachycladus laevispirulifer, that has shown significant antifungal and nematocidal activity. 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 acid mediated cyclisation reaction between 3,4-Dimethylpent-4-en-2-ol and trans-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.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available