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Title: Synthetic and biosynthetic studies on nitrogen heterocycles
Author: MacKinnon, John W. M.
ISNI:       0000 0001 3615 6072
Awarding Body: University of Glasgow
Current Institution: University of Glasgow
Date of Award: 1976
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The reaction of nitrosocarbonyl-compounds with a series of simple dienes to form Diels-Alder adducts has been investigated. The modification of such adducts in further synthesis has been studied and their limitations assessed. A series of adducts, designed for de-acylation under a variety of mild conditions, have been formed from the novel alkyl nitrosoformate reactive intermediates and C-nitroso-formamide adducts have also been briefly examined. The chemistry of adduct formation between ergosteryl acetate and various nitrosocarbonyl-compounds has been examined in detail and a novel rearrangement discovered in this field. The synthesis of a postulated biphenyl intermediate in the biosynthesis of the Amaryllidaceae alkaloids norpluviine and lycorine has been investigated by several different routes. Tracer experiments with 3H- and 14C-tyrosine have confirmed that D- and L-tyrosine are incorporated with equal efficiency into these alkaloids and that D-tyrosine is converted into L-tyrosine before incorporation. The later stages in the biosynthesis of norpluviine and lycorine have been re-examined. A partial retention at position 2 in lycorine of tritium from [3,5-3H2]tyrosine is noted in Clivia miniata Regel and 'Twink' daffodils. Degradation studies suggest that this partial retention results from scrambling of the 2-methylene protons of norpluviine and a mechanism for this is postulated.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available