Biomimetic approaches to tryptophan-derived alkaloids

Marshall, Eve (2017) Biomimetic approaches to tryptophan-derived alkaloids. PhD thesis, University of Nottingham.

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Chapter One describes several natural products derived from the amino acid tryptophan including the structures of the new natural products hyrtioseragamine A and B and tintamine.

Chapter Two describes the work towards hyrtioseragamine A and B. It was intended that the unknown furo[2,3-b]pyrazine-2(1H)-one core would be synthesised from a 1,4-dicarbonyl and this has been synthesised from the amino acid ornithine and the tryptophan derivative kynurenine. Cyclisation of this material to give the 2,3-amino-furan was unsuccessful and thus a number of model systems were synthesised to examine the barrier to furan formation. These models suggest formation of a furan with nitrogen at its 2- and 3-positions was not possible by this route, and further attempts to install a nitrogen to a 2-amino-furan also proved unsuccessful.

Chapter Three describes work on the synthesis of the marine natural product tintamine. This novel compound contains a unique tropo-1,2-dihydro-3,6-phenanthroline core and our synthesis was based on biomimetic principles. A Friedlӓnder reaction allowed successful formation of the quinoline and the attached seven-membered ring was further functionalised to a tropolone. Formation of the dihydro-phenanthroline was successful; it was also possible to separately functionalise the tropolone-quinoline with the sulfur side chain present in tintamine. Unfortunately several of the key intermediates of this route proved unstable, and at this point a final deprotection to form the natural product has not been successful.

Chapter Four contains the synthetic details for the preparation of the novel compounds described in Chapters Two and Three.

Item Type: Thesis (University of Nottingham only) (PhD)
Supervisors: Moody, Christopher J.
Moses, J.
Subjects: Q Science > QP Physiology > QP501 Animal biochemistry
Faculties/Schools: UK Campuses > Faculty of Science > School of Chemistry
Item ID: 41344
Depositing User: Marshall, Eve
Date Deposited: 18 Jul 2017 04:40
Last Modified: 07 May 2020 12:15

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