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Title: The synthesis of hydroxy-iso-evoninic acid via a benzilic ester rearrangement
Author: Warren, Sarah Ann
Awarding Body: Imperial College London
Current Institution: Imperial College London
Date of Award: 2012
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Hydroxy-iso-evoninic acid is a pyridine diacid alkaloid present in nine natural products belonging to the Celastraceae plant family. The relative and absolute stereochemistry of the two stereocentres in this compound, which invariably occurs as a macrocyclic esterifying ligand between the C-3 and C-13 alcohols of β-dihydroagarofuran sesquiterpenes, were not assigned during isolation and no synthesis has yet been reported. The natural products containing hydroxy-iso-evoninic acid are of medicinal interest because of their high anti-HIV activity. This thesis contains an overview of the pyridine alkaloids present in the Celastraceae plant family and background to the benzilic ester rearrangement (BER), a variant of the benzilic acid rearrangement (BAR) discovered by Liebig in 1838. The majority of this thesis describes the first synthesis of the pyridine alkaloid hydroxy-iso-evoninic acid which utilises a BER as the key synthetic step. The development of a tunable diastereoselective BER is also reported, along with the initiation of the development of an asymmetric variant. The synthesis of a model of dihydro-β-agarofuran core euonyminol is also detailed to enable future assignment of the currently unknown stereochemistry of natural hydroxy-iso-evoninic acid.
Supervisor: Spivey, Alan Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available