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Title: The synthesis of mycolic acids
Author: Schubert-Rowles, Richard
ISNI:       0000 0004 2696 6209
Awarding Body: Prifysgol Bangor University
Current Institution: Bangor University
Date of Award: 2010
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The total synthesis of six naturally occuring enantiomerically pure oxygen containing mycolic acids was achieved. The specific mycolic acids synthesized were cis-cyclopropane methoxy-mycolic acid (I) and a-methyl trans-cyclopropane methoxy-mycolic acid (II) of Mycobacterium tuberculosis; and the protected S-a- methyl trans-alkene keto-mycolic acid (III), R-a-methyl trans-alkene keto-mycolic acid (IV), R, R a-methyl trans-alkene hydroxy-mycolic acid (V) and S, S a-methyl trans-alkene hydroxy-mycolic acid (VI) of Mycobacterium marinum. Novel routes in the preparation of the first synthetic a-methyl trans-alkene mycolic acids are discussed, utilising methods such as the modified Julia-Kocienski olefination, the Horner-Wadsworth-Emmons reaction and the Michael addition.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available