This thesisd escribess yntheticw ork carriedo ut on two separatep rojects. (i) Synthetics tudiest owardst he total synthesiso f galanthamine (ii) The total synthesis of 2-Benzoyl-9-azabicyclo[4.2.1 ]non-2-ene Galanthamine is an amaryllidaceae alkaloid processing a rigid tetracyclic structure with a fused dihydrobenzofuran onto a cyclohexenol and a bridging tertiary amine. 2-Benzoyl-9-azabicyclo[4.2.1]non-2-ene is an analogue of anatoxin-a, whereby the acetyl side chain has been substituted with a benzoyl group. Anatoxin-a itself possesses a 9-azabicyclo[4.2.1]nonane framework. Although structurally very different they both share a common feature in that they interact with acetylcholine receptors. Hence chapter 1 is an introduction to Alzheimer's disease which is primarily caused by a lack of acetylcholine. A literature review of the total syntheses of galanthamine and a background of galanthamine is described in chapter 2, whilst chapter 3 details the forward synthesis to the galanthamine framework but with a cyclopentenyl instead of a cyclohexenyl moiety and subsequent attempts for the elaboration of the cyclopentenyl into its corresponding cyclohexenyl moiety. Chapter 4 and 5 describes the published total syntheses of anatoxin-a and analogues of anatoxin-a, whilst chapter 6 concludes the total synthesis of the phenyl analogue of anatoxin-a via a key selenium mediated transannular cyclisation of a Boc-(3-Lactam to furnish the 9-azabicyclo[4.2. l]nonane ring system.
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:289225 |
| Date | January 2002 |
| Creators | Sumoreeah, Ravi Leckman |
| Publisher | University of Sussex |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
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