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Title: Rhodotorula rubra CBS 6469 mediated reduction of carbon-carbon double bonds
Author: McGuinn, John Stephen
Awarding Body: University of Edinburgh
Current Institution: University of Edinburgh
Date of Award: 1998
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A range of compounds designed around a template based upon (Z)-5-benzylidene thiazolidine-2,4-dione were synthesised by Knoevenagel condensation. These were screened against Rhodotorula rubra CBS 6469, a red yeast, using a modification of a process developed by SmithKline Beecham. This has allowed the construction of a 'map' defining the structural features of the template which are required to afford reduction of the carbon-carbon double bond. It has been shown that X1 and X2 must be S and O respectively whilst R3 can be methyl or benzyl. Alkyl substitution at R2 is not tolerated but a variety of substituents can be present at R1. Para groups can be accommodated at R1, but only methyl in the alkyl series, as well as the meta methoxy group. It has also been shown that replacement of the phenyl ring with a cyclohexyl moiety still allows reduction to take place. (Fig. 10893A). Relative reaction rates are also discussed along with the development of a process to afford reduction using Rhodotorula rubra CBS 6469 immobilised in calcium alginate beads. By carrying out reductions on deuterated compounds, and in deuterated media, steps have been taken towards the elucidation of the mechanism of reduction. The following scheme is proposed as a possible mechanistic pathway.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available