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Studies towards the total synthesis and structural elucidation of leiodolide A
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dc.contributor.advisor | Florence, Gordon John | |
dc.contributor.author | Aldred, Gregory | |
dc.coverage.spatial | xiv, 218 p. | en_US |
dc.date.accessioned | 2015-05-19T08:25:42Z | |
dc.date.available | 2015-05-19T08:25:42Z | |
dc.date.issued | 2015-06-24 | |
dc.identifier | uk.bl.ethos.647810 | |
dc.identifier.uri | https://hdl.handle.net/10023/6657 | |
dc.description.abstract | In 2006, the secondary metabolite leiodolide A was isolated from a newly discovered deep-sea sponge of the genus Leiodermatium. The 19-membered macrolide represented a new class of mixed polyketide, nonribosomal, peptide synthetase natural products. A total synthesis of leiodolide A is yet to be achieved and is of specific interest, not only for its complex structure and undefined stereochemistry, but also the potent cytotoxic properties it possesses, particularly towards leukaemia, non-small cell lung and ovarian cancers. A synthetic strategy for leiodolide A must be flexible to overcome the currently unresolved stereochemistry and a convergent route towards the synthesis of the molecule required three subunits. Following the earlier synthesis of the C21-C25 vinyl stannane fragment, this work describes the synthesis of the C1-C10 subunit in the both possible diastereomeric forms. The synthesis of the two required C13 epimers of the C11-C20 subunit is also detailed accompanied by an investigation into potential fragment coupling, in preparation for total synthesis. | en_US |
dc.language.iso | en | en_US |
dc.publisher | University of St Andrews | |
dc.rights | Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International | |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/4.0/ | |
dc.subject | Natural product | en_US |
dc.subject | Organic chemistry | en_US |
dc.subject | Chemistry | en_US |
dc.subject | Synthesis | en_US |
dc.subject.lcc | QP752.P65A6 | |
dc.subject.lcsh | Polyketides | en_US |
dc.subject.lcsh | Natural products--Synthesis | en_US |
dc.subject.lcsh | Lactones | en_US |
dc.subject.lcsh | Chemistry, Organic | en_US |
dc.title | Studies towards the total synthesis and structural elucidation of leiodolide A | 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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