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New routes to indolizidine alkaloids: The total synthesis of (-)-grandisine B

Cuthbertson, James D (2011) New routes to indolizidine alkaloids: The total synthesis of (-)-grandisine B. PhD thesis, University of York.

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Abstract

The plant family Elaeocarpaceae has been the source of a plethora of structurally related alkaloids isolated over the last 50 years. This Thesis describes our synthetic approaches to (−)-grandisine B I, a bioactive indolizidine alkaloid isolated from Elaocarpus grandis in 2005. An overview of alkaloids isolated from the family Elaeocarpaceae is provided and preliminary studies into the synthesis of grandisine B I are described (Chapters 1 and 2). Novel routes to bicyclic lactams II and isoquinuclidinone frameworks III have been developed using aqueous ammonia in a one-pot amination/cyclisation sequence (Chapters 3 and 4). The scope of the developed methodology was initially demonstrated with a concise synthesis of the alkaloid (−)-mearsine V. A biomimetic synthesis of (±)-grandisine B I, using the alkaloid grandisine D IV as a synthetic precursor, is then described in Chapter 5. The development of a formic acid mediated alkyne/acetal cyclisation for the synthesis of heterocyclic scaffolds is also reported. The scope and limitations of the methodology are discussed and applications of the methodology in the synthesis of (−)-grandisine B I and structurally related Elaeocarpus alkaloids are described (Chapter 6).

Item Type: Thesis (PhD)
Keywords: Grandisine B, Indolizidine, Ammonia, Mearsine, Formic acid, Cyclisation
Academic Units: The University of York > Chemistry (York)
Depositing User: Mr James D Cuthbertson
Date Deposited: 17 Jan 2012 12:06
Last Modified: 08 Aug 2013 08:47
URI: http://etheses.whiterose.ac.uk/id/eprint/1970

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