Asymmetric Synthesis of Goniodiol Intermediates

Show simple item record

dc.contributor.advisor Rutledge, Stew en
dc.contributor.author Dansted, Paul Christian en
dc.date.accessioned 2007-07-05 en
dc.date.available 2007-07-05 en
dc.date.issued 2000 en
dc.identifier THESIS 00-017 en
dc.identifier.citation Thesis (PhD--Chemistry)--University of Auckland, 1999 en
dc.identifier.uri http://hdl.handle.net/2292/633 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 https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm en
dc.title Asymmetric Synthesis of Goniodiol Intermediates en
dc.type Thesis en
thesis.degree.discipline Chemistry en
thesis.degree.grantor The University of Auckland en
thesis.degree.level Doctoral en
thesis.degree.name PhD en
dc.rights.holder Copyright: The author en


Files in this item

Find Full text

This item appears in the following Collection(s)

Show simple item record

Share

Search ResearchSpace


Browse

Statistics