Synthetic methods directed towards the synthesis of rapamycin
Synthetic methods directed towards the synthesis of rapamycin
The main contributions of the work described in this thesis are the development of a novel method for N-acylation of Oppolzers bornane-2,10-sultam and some of the Evans oxazolidinones involving N-silyl activation coupled with copper (II) chloride redox catalysis in the acylation reaction to afford the desired products in good yield.
A method was also developed for the suppression of radical induced polymerisation catalysed by EtAlCl2 by galvinoxyl in the asymmetric Diels-Alder reaction. The above methods have then been combined to provide a large scale and efficient preparation of (R)-cyclohex-3-enecarboxylic acid. It is likely that these discoveries will have a wider scope in asymmetric Diels-Alder chemistry involving other chiral auxiliaries, dienes, dienophiles and catalysts. The (R)-cyclohex-3-enecarboxylic acid was then elaborated to form the basis for the preparation of the C30-C42 fragment of rapamycin through the application of Evans technology.
University of Southampton
1994
Thom, Catriona
(1994)
Synthetic methods directed towards the synthesis of rapamycin.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
The main contributions of the work described in this thesis are the development of a novel method for N-acylation of Oppolzers bornane-2,10-sultam and some of the Evans oxazolidinones involving N-silyl activation coupled with copper (II) chloride redox catalysis in the acylation reaction to afford the desired products in good yield.
A method was also developed for the suppression of radical induced polymerisation catalysed by EtAlCl2 by galvinoxyl in the asymmetric Diels-Alder reaction. The above methods have then been combined to provide a large scale and efficient preparation of (R)-cyclohex-3-enecarboxylic acid. It is likely that these discoveries will have a wider scope in asymmetric Diels-Alder chemistry involving other chiral auxiliaries, dienes, dienophiles and catalysts. The (R)-cyclohex-3-enecarboxylic acid was then elaborated to form the basis for the preparation of the C30-C42 fragment of rapamycin through the application of Evans technology.
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Published date: 1994
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Local EPrints ID: 462841
URI: http://eprints.soton.ac.uk/id/eprint/462841
PURE UUID: cc96921d-5d1d-4e55-82e5-615fefbc876c
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Date deposited: 04 Jul 2022 20:14
Last modified: 04 Jul 2022 20:14
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Author:
Catriona Thom
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