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Synthesis of the originally proposed structure of palmerolide C
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dc.contributor.advisor | Florence, Gordon John | |
dc.contributor.author | Wlochal, Joanna | |
dc.coverage.spatial | xii, 225 | en_US |
dc.date.accessioned | 2013-06-11T10:22:03Z | |
dc.date.available | 2013-06-11T10:22:03Z | |
dc.date.issued | 2012 | |
dc.identifier | uk.bl.ethos.574777 | |
dc.identifier.uri | https://hdl.handle.net/10023/3663 | |
dc.description.abstract | The 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.iso | en | en_US |
dc.publisher | University of St Andrews | |
dc.subject.lcc | RM666.M25W6 | |
dc.subject.lcsh | Macrolide antibiotics--Synthesis | en_US |
dc.title | Synthesis of the originally proposed structure of palmerolide C | en_US |
dc.type | Thesis | en_US |
dc.contributor.sponsor | Engineering and Physical Sciences Research Council (EPSRC) | en_US |
dc.type.qualificationlevel | Doctoral | en_US |
dc.type.qualificationname | PhD Doctor of Philosophy | en_US |
dc.publisher.institution | The University of St Andrews | en_US |
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