Studien zur Totalsynthese von Collinolacton & Synthese eines funktionalisierten Cyclooctins
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Philipps-Universität Marburg
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Abstract
In this work studies towards the first total synthesis of the bacterial secondary metabolite Collinolactone are described. The natural product shows a unique 6-10-7 tricyclic ring system of which the two smaller rings contain lactones while flanking a substituted cyclodecatriene. Due to the hindered flexibility in the system, Collinolactone exists as a mixture of rotational isomers. Collinolactone shows biological activity and has the ability to unwind amyloid plaques and proteins that are considered to cause Alzheimers disease. Therefore, the finding of a synthetic approach to the natural product is not only interesting by means of structural challenges, but also for biomedicinal purpose.
Synthetically, the natural product was planned to be built up via a Zweifel-Olefination of the two smaller ring systems. In that way, a precursor should be formed that allows the build-up of the tricyclic backbone. So, the initially followed strategy was the connection of the two smaller rings followed by the synthesis of the larger cyclodecatriene on late stage. After this approach had failed, an alternative way for connecting the building blocks was achieved via an allylation of two modified blocks. In cooperation with other group members, the synthesis of the 6-10-7 ringsystem could be achieved. However, final synthetic transformations failed and the natural product could not be successfully synthesized.
In another part of the thesis, a synthetic route to a functionalized cyclooctyne is described that was supposed to be connected to the Si(001)-surface in cooperation with the Höfer group (Philipps-Univeristät Marburg, physics department). Hereby, the optoelectronical characteristics of the Si(001)-surface should be examined.
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Created: 2022Issued: 2023-03-09Updated: 2023-03-09
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Fachbereich Chemie
Publisher
Philipps-Universität Marburg
Language
ger
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DoctoralThesis
Keywords
studies towards a first synthetic approach towards the bacterial metabolite Collinolactone are described. In additionIn this worka synthetic route
DFG-subjects
Collinolacton Totalsynthese Naturstoffsynthese Cyclooctin
DDC-Numbers
540
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Klangwart, Niklas: Studien zur Totalsynthese von Collinolacton & Synthese eines funktionalisierten Cyclooctins. : Philipps-Universität Marburg 2023-03-09. DOI: https://doi.org/10.17192/z2023.0085.
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This item has been published with the following license: In Copyright