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Title: Studies in marine chemistry and the intramolecular Diels-Alder reaction
Author: Ford, S.
Awarding Body: University College of Swansea
Current Institution: Swansea University
Date of Award: 1983
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Section One (Part One): The assay of the principal green integumentary pigments of the proboscis, body wall and viscera of adult female Bonellla viridis, Rolando (1822) (from Marsaxlokk Bay, Malta) as their dimethyl esters. Bonellin was confirmed as the principal pigment in the proboscis, and also in the body wall and viscera. No other porphyrin pigments were observed in the viscera and stomach contents. Pure bonellin (350mg) was prepared for pharmaceutical screening. Section One (Part Two): The development of synthetic strategies for bonellin. Two chiral pyrrolidone, synthones for ring D of bonellin were prepared from natural camphor. Also discussed is the work of a colleague Dr. Roberts into nucleophilic substitution in AI-pyrrolines and an approach to bonellin from natural heamin. Section Two: A study of the intremolecular Dials-Alder reaction of heterocycle substrates. This section is totally unrelated to section one (parts one and two). Several furans, thiophenes and a pyrrole compound were prepared to investigate the utility of certain bridges between the diene and dienophile moieties. The reluctance of furans with oxygen bridges (ethers, esters and anhydrides) to cyclise is confirmed. Thiophenes with nitrogen bridges (amides, amines, quaternary salt) did not cyclise on heating (reflux, sealed tube) or treatment with S-oxidation or S-methylation reagents. The use of high pressures or activating substituents is recommended for cyclising thiophenes. No adduct was obtained from the pyrrole.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available