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Title: Synthesis of polyfunctionalised cyclopentanes
Author: Hui, Andrew W. H.
Awarding Body: University of Oxford
Current Institution: University of Oxford
Date of Award: 1995
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This thesis describes the syntheses of some polyfunctionalised cyclopentanes via intramolecular aldol condensations of sugar δ-lactone precursors. The known azido carbpcycle (1S,2R,3S,4R,5R)-methyl [5-azido-1,2,3,4- tetrahydrpxy-2,3-O-isopropylidene-cyclopentane] carboxylate was prepared from 2- deoxy-2-iodo-3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heptono-1,5-lactone in five steps. The key reaction was a base-induced intramolecular aldol cyclisation of a 5- iodo-formyl-2,6-lactone. Borohydride reduction of the methyl ester gave an azido triol. Deprotection followed by reduction of the azide functionality produced an amino pentol. The analogous tetrahydroxy β-amino acid was synthesised from the azido carbocycle in three steps. The inhibitory activity of the amino pentol against human liver glycosidases is reported. Two azido bicyclic lactones, (1R,4R,5R,6R,7R)-4-azido-5,6,7-trihydroxy-5,6-0- isopropylidene-2-oxa-bicyclo[2.2.1]heptan-3-one and (1S,4S,5R,6R,7R)-4-azido- 5,6,7-trmydroxy-5,6-O-isopropydilene-2-oxa-bicyclo[2.2.1]heptan-3-one, were prepared from 3,4:6,7-di-O<./em>-isopropylidene-D-glycero-D-talo-heptono-1,5-lactone in five steps. The (1R,4R,5R,6R,7
Supervisor: Fleet, G. W. H. Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Aldol condensation ; Lactones Chemistry, Organic