Asymmetric Synthesis of Goniodiol Intermediates

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dc.contributor.advisor Rutledge, Stew en Dansted, Paul Christian en 2007-07-05 en 2007-07-05 en 2000 en
dc.identifier THESIS 00-017 en
dc.identifier.citation Thesis (PhD--Chemistry)--University of Auckland, 1999 en
dc.identifier.uri en
dc.description Full text is available to authenticated members of The University of Auckland only. en
dc.description.abstract Enantioselective formal syntheses of both the Goniothalamus amuyon metabolite (+)-goniodiol-8-monoacetate 1 and its enantiomer were achieved. Access to the Goniothalamus metabolites (+)-goniotriol 2 and (+)-goniofufurone 5 and their enantiomers was accomplished by the same route. A method was developed to transform threo diols into their erythro counterparts with complete retention of enantiopurity by selective inversion of one stereocentre using the Prévost solvolysis reaction. The meso problem inherent in the Sharpless asymmetric dihydroxylation of Z-alkenes was thereby circumvented. This method was demonstrated using enantioenriched diols derived from Sharpless asymmetric dihydroxylation of several alkenes. Menthyl cinnamate 135 was investigated as a substrate with pre-existing chirality to determine the merits of double diastereoselection for application in the synthesis of Goniothalamus metabolites. A mechanistic insight allowed simplification of the Prévost solvolysis method to a one-pot procedure requiring only mild reaction conditions. en
dc.language.iso en en
dc.publisher ResearchSpace@Auckland en
dc.relation.ispartof PhD Thesis - University of Auckland en
dc.relation.isreferencedby UoA9989371214002091 en
dc.rights Restricted Item. Available to authenticated members of The University of Auckland. en
dc.rights Items in ResearchSpace are protected by copyright, with all rights reserved, unless otherwise indicated. en
dc.rights.uri en
dc.title Asymmetric Synthesis of Goniodiol Intermediates en
dc.type Thesis en Chemistry en The University of Auckland en Doctoral en PhD en
dc.rights.holder Copyright: The author en
dc.identifier.wikidata Q112902228

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