Stereoselective semisynthesis of uzarigenin and allo -uzarigenin
| Autor: | Sarah Al Muthafer, Christoph Schissler, Vanessa Koch, Hannes Kühner, Martin Nieger, Stefan Bräse |
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| Jazyk: | angličtina |
| Rok vydání: | 2023 |
| Předmět: | |
| Zdroj: | Organic Chemistry Frontiers |
| ISSN: | 2052-4110 2052-4129 |
| DOI: | 10.5445/ir/1000156349 |
| Popis: | Herein, we report the concise semisynthesis of the natural cardenolide uzarigenin and its diastereoisomer allo-uzarigenin in nine and seven steps, respectively, starting from the broadly available epi-androsterone. For this purpose, the synthetic strategy for the stereoselective introduction of the β-hydroxy group at C-14 via Mukaiyama oxidation is discussed. Additionally, the installation of the butenolide ring at C-17 is performed using a Stille-cross-coupling reaction with subsequent stereoselective hydrogenation of the C-16/C-17 double bond to exclusively give allo-uzarigenin. By directing the hydrogenation via a protecting group strategy, the C-17β isomer can also be obtained stereoselectively. |
| Databáze: | OpenAIRE |
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