Stereocontrolled synthesis of proto-quercitol and of aminocyclitol precursors

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dc.contributor.advisor Rutledge, P.S.(Stew) en
dc.contributor.author Renner, Noel David en
dc.date.accessioned 2007-09-10T10:44:14Z en
dc.date.available 2007-09-10T10:44:14Z en
dc.date.issued 1990 en
dc.identifier THESIS 90-168 en
dc.identifier.citation Thesis (PhD--Chemistry)--University of Auckland, 1990 en
dc.identifier.uri http://hdl.handle.net/2292/1811 en
dc.description Restricted Item. Print thesis available in the University of Auckland Library or may be available through Interlibrary Loan. en
dc.description.abstract A total synthesis of the naturally occurring cyclohexenetetrol conduritol A from p-benzoquinone was achieved in four steps with total stereoselectivity in 55% overall yield. Hydroboration of the tetrabenzoate ester of conduritol A gave racemic proto-quercitol stereoselectively. In a stereoselective nine step synthesis p-benzoquinone was also converted to an aminocyclitol precursor. This work featured a stereospecific vanadium catalysed epoxidation of an allylic alcohol to complete the sequence, which constituted a formal total synthesis of the aminocyclitol 3-O-demethylfortamine. Preliminary investigations were also made toward introducing chirality into this sequence by enantiotopic differentiation of symmetrical compounds. An investigation into the potential of p-benzoquinone monoxime as an aminocyclitol precursor was also initiated. en
dc.language.iso en en
dc.publisher ResearchSpace@Auckland en
dc.relation.ispartof PhD Thesis - University of Auckland en
dc.relation.isreferencedby UoA9939720314002091 en
dc.rights Restricted Item. Print thesis available in the University of Auckland Library or may be available through Interlibrary Loan. en
dc.rights.uri https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm en
dc.title Stereocontrolled synthesis of proto-quercitol and of aminocyclitol precursors 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
dc.rights.accessrights http://purl.org/eprint/accessRights/ClosedAccess en


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