Traceless Solid-Phase Synthesis of Ketones via Acid-Labile Enol Ethers: Application in the Synthesis of Natural Products and Derivatives
In solid-phase organic synthesis, Wang resin is traditionally used for the immobilization of acids, alcohols, phenols, and amines. We report the use of Wang resin for the traceless synthesis of ketones via acid-labile enol ethers. We demonstrate the practicality of this synthetic strategy on the sol...
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| Format: | Article |
| Language: | English |
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MDPI AG
2019-04-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/24/7/1406 |
| _version_ | 1818420808072036352 |
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| author | Eva Schütznerová Anna Krchňáková Viktor Krchňák |
| author_facet | Eva Schütznerová Anna Krchňáková Viktor Krchňák |
| author_sort | Eva Schütznerová |
| collection | DOAJ |
| description | In solid-phase organic synthesis, Wang resin is traditionally used for the immobilization of acids, alcohols, phenols, and amines. We report the use of Wang resin for the traceless synthesis of ketones via acid-labile enol ethers. We demonstrate the practicality of this synthetic strategy on the solid-phase synthesis of pyrrolidine-2,4-diones, which represent the core structure of several natural products, including tetramic acid. Base-triggered condensation of pyrrolidine-2,4-diones yielded 4-hydroxy-1,1′,2′,5-tetrahydro-2<i>H</i>,5′<i>H</i>-[3,3′-bipyrrole]-2,5′-diones. |
| first_indexed | 2024-12-14T13:00:21Z |
| format | Article |
| id | doaj.art-d29bbac36d014928bf955f96b5863377 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-14T13:00:21Z |
| publishDate | 2019-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-d29bbac36d014928bf955f96b58633772022-12-21T23:00:28ZengMDPI AGMolecules1420-30492019-04-01247140610.3390/molecules24071406molecules24071406Traceless Solid-Phase Synthesis of Ketones via Acid-Labile Enol Ethers: Application in the Synthesis of Natural Products and DerivativesEva Schütznerová0Anna Krchňáková1Viktor Krchňák2Department of Organic Chemistry, Faculty of Science, Palacký University, 17. listopadu 12, 771 46 Olomouc, Czech RepublicDepartment of Chemistry and Biochemistry, 251 Nieuwland Science Center, University of Notre Dame, Notre Dame, IN 46556, USADepartment of Organic Chemistry, Faculty of Science, Palacký University, 17. listopadu 12, 771 46 Olomouc, Czech RepublicIn solid-phase organic synthesis, Wang resin is traditionally used for the immobilization of acids, alcohols, phenols, and amines. We report the use of Wang resin for the traceless synthesis of ketones via acid-labile enol ethers. We demonstrate the practicality of this synthetic strategy on the solid-phase synthesis of pyrrolidine-2,4-diones, which represent the core structure of several natural products, including tetramic acid. Base-triggered condensation of pyrrolidine-2,4-diones yielded 4-hydroxy-1,1′,2′,5-tetrahydro-2<i>H</i>,5′<i>H</i>-[3,3′-bipyrrole]-2,5′-diones.https://www.mdpi.com/1420-3049/24/7/1406solid-phase synthesisketonetraceless synthesisnatural productsenol ethers |
| spellingShingle | Eva Schütznerová Anna Krchňáková Viktor Krchňák Traceless Solid-Phase Synthesis of Ketones via Acid-Labile Enol Ethers: Application in the Synthesis of Natural Products and Derivatives Molecules solid-phase synthesis ketone traceless synthesis natural products enol ethers |
| title | Traceless Solid-Phase Synthesis of Ketones via Acid-Labile Enol Ethers: Application in the Synthesis of Natural Products and Derivatives |
| title_full | Traceless Solid-Phase Synthesis of Ketones via Acid-Labile Enol Ethers: Application in the Synthesis of Natural Products and Derivatives |
| title_fullStr | Traceless Solid-Phase Synthesis of Ketones via Acid-Labile Enol Ethers: Application in the Synthesis of Natural Products and Derivatives |
| title_full_unstemmed | Traceless Solid-Phase Synthesis of Ketones via Acid-Labile Enol Ethers: Application in the Synthesis of Natural Products and Derivatives |
| title_short | Traceless Solid-Phase Synthesis of Ketones via Acid-Labile Enol Ethers: Application in the Synthesis of Natural Products and Derivatives |
| title_sort | traceless solid phase synthesis of ketones via acid labile enol ethers application in the synthesis of natural products and derivatives |
| topic | solid-phase synthesis ketone traceless synthesis natural products enol ethers |
| url | https://www.mdpi.com/1420-3049/24/7/1406 |
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