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Towards the Synthesis of Hybrid Peloruside A and Laulimalide Analogues

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dc.contributor.advisor Harvey, Joanne
dc.contributor.advisor Teesdale-Spittle, Paul
dc.contributor.author Tho, Febly
dc.date.accessioned 2010-11-24T21:17:53Z
dc.date.accessioned 2022-10-25T00:38:33Z
dc.date.available 2010-11-24T21:17:53Z
dc.date.available 2022-10-25T00:38:33Z
dc.date.copyright 2010
dc.date.issued 2010
dc.identifier.uri https://ir.wgtn.ac.nz/handle/123456789/22690
dc.description.abstract (+)-Peloruside A is a novel cytotoxic marine natural product isolated from the New Zealand sponge Mycale hentscheli(42). Peloruside A is a potential anticancer agent that has a similar mode of action to that of the successful drug paclitaxel. Biological analysis indicated that (+)-peloruside A promotes tubulin hyperassembly and cellular microtubule stabilisation which lead to mitosis blockage in the G2/M phase of the cell cycle and consequent cell apoptosis(43),(47). (-)-Laulimalide is also a cytotoxic natural product with microtubule stabilising bioactivity, and is a potential anticancer agent(47). Biological analysis showed that (+)-peloruside A and (-)-laulimalide are competitive, suggesting that they bind to the same active site(47). (+)-Peloruside A and (-)-laulimalide also display synergy with taxoids(47). Due to the structural complexity of peloruside A, our research has focused on developing an analogue 151 for ease of synthesis. Thus, the simplified C5-C9 dihydropyran moiety of (-)-laulimalide, with fewer stereocentres than that of (+)-peloruside A, has been incorporated into analogue 151 whilst retaining the 16- membered ring backbone of (+)-peloruside A. The proposed synthesis of 151 involves a Yamaguchi macrolactonization, a 1,5-anti-aldol coupling, and a ring closing metathesis as key reactions. This thesis reports on the synthesis of key fragments of analogue 151 and the crucial 1,5-anti-aldol coupling reaction for the assembly of the carbon backbone. en_NZ
dc.format pdf en_NZ
dc.language en_NZ
dc.language.iso en_NZ
dc.publisher Te Herenga Waka—Victoria University of Wellington en_NZ
dc.subject Microtubules en_NZ
dc.subject Cancer research en_NZ
dc.title Towards the Synthesis of Hybrid Peloruside A and Laulimalide Analogues en_NZ
dc.type Text en_NZ
vuwschema.contributor.unit School of Biological Sciences en_NZ
vuwschema.subject.marsden 250302 Biological and Medical Chemistry en_NZ
vuwschema.subject.marsden 250301 Organic Chemical Synthesis en_NZ
vuwschema.type.vuw Awarded Research Masters Thesis en_NZ
thesis.degree.discipline Biomedical Science en_NZ
thesis.degree.grantor Te Herenga Waka—Victoria University of Wellington en_NZ
thesis.degree.level Masters en_NZ
thesis.degree.name Master of Biomedical Science en_NZ

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