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dc.contributor.advisorFlorence, Gordon John
dc.contributor.authorWlochal, Joanna
dc.coverage.spatialxii, 225en_US
dc.date.accessioned2013-06-11T10:22:03Z
dc.date.available2013-06-11T10:22:03Z
dc.date.issued2012
dc.identifieruk.bl.ethos.574777
dc.identifier.urihttp://hdl.handle.net/10023/3663
dc.description.abstractThe palmerolides are an emerging class of polyketide natural products isolated from marine organisms inhabiting the Antarctic Sea. Although there has been a substantial effort to prepare the most active family member palmerolide A, no synthetic work has been performed in the area of the other members of the family; palmerolides B and C of different ring structure. These compounds are particularly interesting due to their complex structures with undefined stereochemistry and both display high selectivity towards human melanoma cancer cell lines. A highly convergent strategy to access palmerolide C has been developed, relying on the assembly of three fragments using key bond couplings at C6-C7 (boron-mediated aldol reaction/dehydration) and C14-C15 (Julia-Kocienski olefination), followed by a suitable macrolactonisation step and Buchwald enamide formation. Prior to subunit synthesis, the relative configuration of the C8-C10 stereotriad was resolved via the synthesis of diastereomeric degradation fragments by the application of organocatalytic cross aldol reactions and a suitable 1,3-selective reduction.en_US
dc.language.isoenen_US
dc.publisherUniversity of St Andrews
dc.subject.lccRM666.M25W6
dc.subject.lcshMacrolide antibiotics--Synthesisen_US
dc.titleSynthesis of the originally proposed structure of palmerolide Cen_US
dc.typeThesisen_US
dc.contributor.sponsorEngineering and Physical Sciences Research Council (EPSRC)en_US
dc.type.qualificationlevelDoctoralen_US
dc.type.qualificationnamePhD Doctor of Philosophyen_US
dc.publisher.institutionThe University of St Andrewsen_US


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