The preparation of an advanced intermediate on route towards the synthesis of tedanolide C is reported here. It is based on the coupling of two fragments of similar size and complexity, which in turn are prepared by highly stereoselective substrate-controlled titanium-mediated aldol reactions from chiral ketones.
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Development of the Synthesis of Desepoxy-Tedanolide C.
J Org Chem
February 2024
Institute of Organic Chemistry, Gottfried Wilhelm Leibniz Universität Hannover, Schneiderberg 1B, 30167Hannover, Germany.
We are presenting the development of our route for the total synthesis of desepoxy-tedanolide C. Through the obtained analytical data, the proposed structure of tedanolide C is questioned and a different configuration for this natural product is proposed. Key steps of the synthesis are a Kiyooka aldol reaction that builds up the tertiary alcohol flanked by three oxygenated carbon atoms and two aldol reactions used for fragment couplings.
View Article and Find Full Text PDFNatural products as drugs and tools for influencing core processes of eukaryotic mRNA translation.
Pharmacol Res
August 2021
Institute of Pharmaceutical Biology, Faculty of Biochemistry, Chemistry and Pharmacy, Goethe University, Frankfurt, Germany; LOEWE Center for Translational Biodiversity Genomics (LOEWE-TBG), Frankfurt, Germany.
Eukaryotic protein synthesis is the highly conserved, complex mechanism of translating genetic information into proteins. Although this process is essential for cellular homoeostasis, dysregulations are associated with cellular malfunctions and diseases including cancer and diabetes. In the challenging and ongoing search for adequate treatment possibilities, natural products represent excellent research tools and drug leads for new interactions with the translational machinery and for influencing mRNA translation.
View Article and Find Full Text PDFSynthesis of Desepoxy-Tedanolide C.
Chemistry
April 2021
Institute of Organic Chemistry, Gottfried Wilhelm Leibniz Universität Hannover, Schneiderberg 1B, 30167, Hannover, Germany.
The synthesis of desepoxy-tedanolide C was accomplished and provided experimental evidence on the configuration of tedanolide C. The reported chemical shifts and coupling constants point to a configuration different from the published structure and analogous to the structures of the other members of this family of natural products. The key step is a Kiyooka aldol protocol for the stereoselective synthesis of the tertiary alcohol flanked by three additional oxygenated carbon atoms.
View Article and Find Full Text PDFInvestigations on the mode of action of gephyronic acid, an inhibitor of eukaryotic protein translation from myxobacteria.
PLoS One
February 2019
Department of Chemical Biology, Helmholtz Centre for Infection Research, Braunschweig, Germany.
The identification of inhibitors of eukaryotic protein biosynthesis, which are targeting single translation factors, is highly demanded. Here we report on a small molecule inhibitor, gephyronic acid, isolated from the myxobacterium Archangium gephyra that inhibits growth of transformed mammalian cell lines in the nM range. In direct comparison, primary human fibroblasts were shown to be less sensitive to toxic effects of gephyronic acid than cancer-derived cells.
View Article and Find Full Text PDFStudies towards the synthesis of tedanolide C. Construction of the C13-epi C1-C15 fragment.
Org Biomol Chem
June 2016
Secció de Química Orgànica, Departament de Química Inorgànica i Orgànica, and Institut de Biomedicina de la Universitat de Barcelona (IBUB), Universitat de Barcelona, Carrer Martí i Franqués 1-11, 08028 Barcelona, Catalonia, Spain.
The preparation of an advanced intermediate on route towards the synthesis of tedanolide C is reported here. It is based on the coupling of two fragments of similar size and complexity, which in turn are prepared by highly stereoselective substrate-controlled titanium-mediated aldol reactions from chiral ketones.
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