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Application of Direct Imine Acylation Methodology in the Synthesis of Nitrogen Heterocycles and Natural Products

Chambers, Sarah (2016) Application of Direct Imine Acylation Methodology in the Synthesis of Nitrogen Heterocycles and Natural Products. PhD thesis, University of York.

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Abstract

This thesis describes the use of direct imine acylation (DIA) methodology in a range of different applications. Firstly, the attempted synthesis of (±)-cytisine is described (Chapter 2). The use of DIA methodology in the formation of the pyridone ring scaffold of (±)-cytisine has been explored. In the most advanced synthesis towards (±)-cytisine achieved in this project, the generation of N-acyliminium ions from imine A and subsequent nucleophilic addition of organometallic allyl reagents was developed to give diene B. DIA methodology has also been utilised in the synthesis of spirocyclic products from simple indole acids C and imines D (Chapter 3). The reaction provides a broad range of products E in good yields and the indole acid starting materials C are readily synthesised using Fischer indole methodology. The stereoselectivity of the reaction, derivatisation of the products E and 3D shape analysis are also described. Finally, work towards the synthesis of (±)-aspidospermidine, using the spirocyclisation methodology developed in this project, is introduced (Chapter 4). Two strategies are proposed utilising an intramolecular Heck reaction or a ring-closing metathesis to complete the polycyclic scaffold. A key DIA reaction between the synthesised acid F and imine G is reported and shows formation of the spirocyclic scaffold H.

Item Type: Thesis (PhD)
Related URLs:
Academic Units: The University of York > Chemistry (York)
Identification Number/EthosID: uk.bl.ethos.713330
Depositing User: Miss Sarah Chambers
Date Deposited: 03 May 2017 15:43
Last Modified: 24 Jul 2018 15:22
URI: http://etheses.whiterose.ac.uk/id/eprint/16948

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