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Title: Applications of a serine derived aldehyde to natural product synthesis
Author: Montgomery, Charles H.
Awarding Body: University of Edinburgh
Current Institution: University of Edinburgh
Date of Award: 2000
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This thesis documents the development of serine derived aldehyde 73 and its application to natural product synthesis. (Fig. 9978A) Highly efficient syntheses of the biologically important natural products DAB1 35 and nectrisine 36 from aldehyde 73 are discussed. The synthesis of these molecules made use of highly efficient asymmetric boron mediated syn aldol reaction to generate a common intermediate, lactam 114. (Fig. 9978B) A alternate synthesis of lactam 114, making use of the Sharpless asymmetric dihydroxylation reaction is also discussed, along with an extension of the aldol reaction methodology which allowed the development of syntheses directed toward the C4Me analogue of 35 and the C3Me analogue of 36. Finally, the utility of aldehyde 73 towards the synthesis of the potential hydantocidin analogues 176 and 181 and the lactacystin analogue 183 was investigated (Fig. 9978C).
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available