Sequential Ketene Generation from Dioxane-4,6-dione-keto-dioxinones for the Synthesis of Terpenoid Resorcylates
| Autor: | Philip J. Parsons, Daniel C. Elliott, Tsz-Kan Ma, Rosa Cookson, Aymane Selmani, Anthony G. M. Barrett |
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| Přispěvatelé: | Commission of the European Communities |
| Rok vydání: | 2016 |
| Předmět: |
Ketene
chemistry.chemical_element Stereoisomerism 010402 general chemistry 01 natural sciences Biochemistry Catalysis Dioxanes chemistry.chemical_compound Organic chemistry Benzopyrans Chromans Physical and Theoretical Chemistry Biological Products Primary (chemistry) Molecular Structure Terpenes 010405 organic chemistry Organic Chemistry Thermal decomposition Aromatization Ethylenes Ketones 0104 chemical sciences chemistry Yield (chemistry) 03 Chemical Sciences Palladium |
| Zdroj: | Organic Letters. 18:1800-1803 |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | Trapping of the ketene generated from the thermolysis of 2-methyl-2-phenyl-1,3-dioxane-4,6-dione-keto-dioxinone at 50 °C with primary, secondary, or tertiary alcohols gave the corresponding dioxinone β-keto-esters in good yield under neutral conditions. These intermediates were converted by palladium(0)-catalyzed decarboxylative allyl migration and aromatization into the corresponding β-resorcylates. These transformations were applied to the syntheses of the natural products (±)-cannabiorcichromenic and (±)-daurichromenic acid. |
| Databáze: | OpenAIRE |
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