Cyclisation strategies towards the synthesis of natural products
Cyclisation strategies towards the synthesis of natural products
This thesis is concerned with the development of cyclisation methodologies which have potential in the synthesis of natural products. A palladium catalysed cyclisation is developed and applied to the synthesis of virola indenone. The structure of virola indenone is redefined and two routes to the natural product are described. A one pot synthesis is also developed. The use of a radical cyclisation methodology utilising thiyl radicals and a bite back strategy to attempt to control the stereoselectivity is studied. Its scope in the synthesis of aryltetralins and other systems is investigated. A new method of synthesising biaryls and triaryls through an intramolecular ipso- substitution reaction initiated by the addition of an aryl radical to a benzyl ether is described. A tandem variant of the reaction is also demonstrated. A literature review of the synthesis of aryl indenones is presented.
University of Southampton
Newman, Nicola Ann
8f0ebe4e-604a-4cb8-a01d-9d38483126c4
2001
Newman, Nicola Ann
8f0ebe4e-604a-4cb8-a01d-9d38483126c4
Newman, Nicola Ann
(2001)
Cyclisation strategies towards the synthesis of natural products.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
This thesis is concerned with the development of cyclisation methodologies which have potential in the synthesis of natural products. A palladium catalysed cyclisation is developed and applied to the synthesis of virola indenone. The structure of virola indenone is redefined and two routes to the natural product are described. A one pot synthesis is also developed. The use of a radical cyclisation methodology utilising thiyl radicals and a bite back strategy to attempt to control the stereoselectivity is studied. Its scope in the synthesis of aryltetralins and other systems is investigated. A new method of synthesising biaryls and triaryls through an intramolecular ipso- substitution reaction initiated by the addition of an aryl radical to a benzyl ether is described. A tandem variant of the reaction is also demonstrated. A literature review of the synthesis of aryl indenones is presented.
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Published date: 2001
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Local EPrints ID: 464389
URI: http://eprints.soton.ac.uk/id/eprint/464389
PURE UUID: d96de29a-9749-4666-9d9b-67c3c2a1c45f
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Date deposited: 04 Jul 2022 23:28
Last modified: 16 Mar 2024 19:28
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Author:
Nicola Ann Newman
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