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Isolation, identification and chemical modification of Narcissus alkaloids
Burke, Edmund William Dwerryhouse
[Thesis]. Manchester, UK: The University of Manchester; 2016.
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Abstract
Isolation, identification and chemical modification of Narcissus alkaloids A submission for the degree of Doctor of Philosophy at the University of Manchester Edmund William Dwerryhouse Burke, 2015 Galanthamine is one of only a few drugs that is licenced for the treatment of Alzheimer’s disease. It is manufactured through an inefficient synthetic process or extracted from members of the Amaryllidaceae plant family. In this work a range of structurally related alkaloids was semisynthesised from galanthamine and used as standards to assist with the search for alkaloids that may make a good starting point in the semisynthesis of galanthamine. The search was targeted on the effluent from the production line of Alzeim Ltd., a company that extracted galanthamine from members of the Narcissus genus. In addition to the above there was an examination of specific areas of galanthamine chemistry; focusing on the application of synthetic methodologies to open new chemical space. By far the most successful of these was the use of galanthamine in a urea-mediated intramolecular aryl migration. A rare example of lithiation chemistry being applied to a natural product and also the most complicated structure to date on which the intramolecular aryl migration has been performed.
Keyword(s)
galanthamine; intramolecular aryl migration; narwedine; norgalanthamine; sanguinine