Strategies towards the synthesis of prostaglandin analogues

 

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dc.contributor.author Haupt, Hayley Claire en_ZA
dc.date.accessioned 2014-08-13T14:26:29Z
dc.date.available 2014-08-13T14:26:29Z
dc.date.issued 2006 en_ZA
dc.identifier.citation Haupt, H. 2006. Strategies towards the synthesis of prostaglandin analogues. University of Cape Town. en_ZA
dc.identifier.uri http://hdl.handle.net/11427/6312
dc.description Includes bibliographical references (leaves 173-179). en_ZA
dc.description.abstract Different strategies for the synthesis of cyclopentenone prostaglandins and their analogues have been explored. The key transformation critical to the success of each of the described routes involves a Lewis-acid mediated retro Diels-Alder (rDA) reaction as the final step in liberating a 4, 5 disubstituted cyclopent-2-ene-1- one under extremely mild conditions. The first approach involves installation of the a-chain followed by base-mediated methodology to affect regiospecific enolate generation. Effective trapping of the enolate generates the requisite target. Within the context of this strategy both 2- and 3-component coupling protocols have been elaborated. Having demonstrated that the a- and p- sidechains could be installed, the key rDA reaction has been used to generate target analogues. The second approach utilizes a Diels-Alder cycloaddition reaction as the key step. The thermal and Lewis-acid catalysed Diels-Alder reactions between tricyclo[5.2.1.0 2,6]dec-8-en-3-one and 3-hydroxytricyclo[5.2.1.0 2,6]dec-8-ene with butadiene and butadiene sulfone have been investigated. While reaction between the enone and the dienophiles proved to be low yielding, the reaction between the allylic alcohol and butadiene sulfone proceeded readily and in high yield. The derived cycloadduct represents a late-stage intermediate for the synthesis of isoprostanes. Methodologies to perform cis-hydroxylation followed by oxidative cleavage of the cyclohexene moiety have been successfully implemented. Finally, a synthesis was designed for generating oxygen analogues of the prostaglandin targets. en_ZA
dc.language.iso eng en_ZA
dc.subject.other Chemistry en_ZA
dc.title Strategies towards the synthesis of prostaglandin analogues en_ZA
dc.type Thesis / Dissertation en_ZA
uct.type.publication Research en_ZA
uct.type.resource Thesis en_ZA
dc.publisher.institution University of Cape Town
dc.publisher.faculty Faculty of Science en_ZA
dc.publisher.department Department of Chemistry en_ZA
dc.type.qualificationlevel Doctoral en_ZA
dc.type.qualificationname PhD en_ZA
uct.type.filetype Text
uct.type.filetype Image


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