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Title: Synthetic methods directed towards the synthesis of rapamycin
Author: Thom, Catriona
ISNI:       0000 0001 3516 9664
Awarding Body: University of Southampton
Current Institution: University of Southampton
Date of Award: 1994
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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.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Organic chemistry