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dc.contributor.advisorGreaney, Mike
dc.contributor.advisorLusby, Paul
dc.contributor.authorShi, Lei
dc.date.accessioned2011-11-25T15:41:18Z
dc.date.available2011-11-25T15:41:18Z
dc.date.issued2011-11-23
dc.identifier.urihttp://hdl.handle.net/1842/5705
dc.description.abstractMerrilactone A (1) was isolated in only 0.004% yield from the methanol extracts of the pericarps of Illicium merrillianum. Structural elucidation of Merrilactone A revealed a compact, cage-like pentacyclic architecture of high molecular complexity, featuring seven stereocentres, five of which as contiguous fully substituted carbon atoms, two γ-lactones and a central oxetane ring. Merrilactone A also exhibits an important neurotrophic activity, significantly promoting neurite outgrowth in the primary cultures of foetal rat cortical neurons at very low concentrations. Structurally, merrilactone A is related to anislactones A and B, a pair of epimeric sesquiterpene dilactones discovered ten years earlier by Kouno and co-workers from the related Illicium anisatum plant. Fukuyama has shown that anislactone B can be converted into merrilactone A using a simple three step sequence, suggesting that the anislactones may be biogenetic precursors to merrilactone A. Described in this thesis are our research efforts directed towards developing a conceptually novel synthetic route enabling regiodivergent total synthesis of both anislactone A / B and merrilactone A. Our synthetic route (around 22 steps) features several key reactions, which include a [2+2] photo-cycloaddition reaction, Tiffeneau-Demjanov ring expansion and titanium(III) mediated radical cyclization.en
dc.contributor.sponsorEngineering and Physical Sciences Research Council (EPSRC)en
dc.contributor.sponsorORSen
dc.language.isoenen
dc.publisherThe University of Edinburghen
dc.subjectnatural productsen
dc.subjecttotal synthesisen
dc.subjectMerrilactoneen
dc.subjectneurite outgrowthen
dc.titleTotal synthesis of (±)-Merrilactone A and (±)-Anislactone Aen
dc.typeThesis or Dissertationen
dc.type.qualificationlevelDoctoralen
dc.type.qualificationnamePhD Doctor of Philosophyen


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