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dc.contributor.advisorGeorge, Jonathan-
dc.contributor.advisorAbell, Andrew David-
dc.contributor.authorPepper, Henry Patrick-
dc.description.abstractSynthetic efforts towards various meroterpenoid natural products based on biosynthetic speculation were undertaken in order to gain biosynthetic insight and to develop efficient syntheses of some structurally complex, biologically active compounds. The first total synthesis of the PPAP natural product garcibracteatone was achieved in four linear steps from phloroglucinol (0.6% overall yield). The key biomimetic synthetic step was an oxidative radical cyclization cascade reaction, where four new carbon-carbon bonds, four new carbocyclic rings and five new stereocentres were formed in the one step. The first total synthesis of merochlorin A was achieved in five linear steps from methyl-3,5- dimethoxyphenylacetate (6% overall yield). The key biomimetic synthetic step was a [5 + 2] cycloaddition reaction induced be oxidative dearomatization to form the bicyclo[3.2.1]octane core. The first total synthesis of the napyradiomycin natural product naphthomevalin was achieved in 11 steps from methyl-3,5-dimethoxyphenylacetate (1.4% overall yield). The key biomimetic synthetic step was a thermal α-ketol rearrangement reaction to form the naphthoquinone core of the napyradiomycins. The synthetic naphthomevalin was additionally converted into A80915G via a biomimetic Sɴ2 epoxidation reaction, and into napyradiomycin A1 via a chemoenzymatic reaction.en
dc.subjectbiomimetic synthesisen
dc.subjectnatural product synthesisen
dc.titleBiomimetic synthesis of meroterpenoid natural products using dearomatization strategiesen
dc.contributor.schoolSchool of Physical Sciencesen
dc.provenanceThis electronic version is made publicly available by the University of Adelaide in accordance with its open access policy for student theses. Copyright in this thesis remains with the author. This thesis may incorporate third party material which has been used by the author pursuant to Fair Dealing exceptions. If you are the owner of any included third party copyright material you wish to be removed from this electronic version, please complete the take down form located at:
dc.description.dissertationThesis (Ph.D.) -- University of Adelaide, School of Physical Sciences, 2016.en
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