Item type:Thesis, Open Access

Totalsynthese von Preussochromon D & Beiträge zur Totalsynthese von Preussochromon E & F

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Date

2020-11-10

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Philipps-Universität Marburg
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Abstract

In this work, the first enantioselective total synthesis of preussochromone D was developed, yielding the preussochromone in 15% overall yield over 9 steps. Key step of the synthesis was a highly diastereoselective intramolecular aldol reaction between a benzylic keton and an α-keto-β-hydroxyester moiety. Besides the natural product, four additional epimers of Preussochromone D and F were synthesized and fully characterized. During the total synthesis of Preussochomone D, multiple highly diastereoselective intramolecular aldol additions and aldol condensations of chromanones to α,β-diketo esters and α-keto- β-hydroxy esters were developed. These implementations allow the stereoselective synthesis of different, highly substituted tetrahydrocyclopenta[b]chromanones and represent a modular synthetic strategy as compared to those known in literature.

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Dates
Created: 2020Issued: 2020-11-10Updated: 2020-11-10
DOI
https://doi.org/10.17192/z2020.0509
Faculty
Fachbereich Chemie
Publisher
Philipps-Universität Marburg
Language
ger
Data types
DoctoralThesis
Keywords
preussochromoneStereoselektivPreussochromoneNatural product synthesisNaturstoffsynthesestereoselektive
DDC-Numbers
540
License
https://rightsstatements.org/vocab/InC-NC/1.0/
URI
https://open.uni-marburg.de/handle/10.17192/z2020.0509
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Kerste, Eric: Totalsynthese von Preussochromon D & Beiträge zur Totalsynthese von Preussochromon E & F. : Philipps-Universität Marburg 2020-11-10. DOI: https://doi.org/10.17192/z2020.0509.

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This item has been published with the following license: In Copyright