Synthesis of Polysubstituted Tetrahydropyrans by Stereoselective Hydroalkoxylation of Silyl Alkenols: En Route to Tetrahydropyranyl Marine Analogues
Tetrahydropyrans are abundantly found in marine natural products. The interesting biological properties of these compounds and their analogues make necessary the development of convenient procedures for their synthesis. In this paper, an atom economy access to tetrahydropyrans by intramolecular acid...
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| Format: | Article |
| Language: | English |
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MDPI AG
2018-11-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/16/11/421 |
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| author | Carlos Díez-Poza Patricia Val Francisco J. Pulido Asunción Barbero |
| author_facet | Carlos Díez-Poza Patricia Val Francisco J. Pulido Asunción Barbero |
| author_sort | Carlos Díez-Poza |
| collection | DOAJ |
| description | Tetrahydropyrans are abundantly found in marine natural products. The interesting biological properties of these compounds and their analogues make necessary the development of convenient procedures for their synthesis. In this paper, an atom economy access to tetrahydropyrans by intramolecular acid-mediated cyclization of silylated alkenols is described. p-TsOH has shown to be an efficient reagent to yield highly substituted tetrahydropyrans. Moreover, excellent diastereoselectivities are obtained both for unsubstituted and alkylsubstituted vinylsilyl alcohols. The methodology herein developed may potentially be applied to the synthesis of marine drugs derivatives. |
| first_indexed | 2024-04-11T21:58:24Z |
| format | Article |
| id | doaj.art-3318ce88b7f44b5b8e99798fa46ba821 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-04-11T21:58:24Z |
| publishDate | 2018-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-3318ce88b7f44b5b8e99798fa46ba8212022-12-22T04:01:01ZengMDPI AGMarine Drugs1660-33972018-11-01161142110.3390/md16110421md16110421Synthesis of Polysubstituted Tetrahydropyrans by Stereoselective Hydroalkoxylation of Silyl Alkenols: En Route to Tetrahydropyranyl Marine AnaloguesCarlos Díez-Poza0Patricia Val1Francisco J. Pulido2Asunción Barbero3Department of Organic Chemistry, Faculty of Science, Campus Miguel Delibes, 47011 Valladolid, SpainDepartment of Organic Chemistry, Faculty of Science, Campus Miguel Delibes, 47011 Valladolid, SpainDepartment of Organic Chemistry, Faculty of Science, Campus Miguel Delibes, 47011 Valladolid, SpainDepartment of Organic Chemistry, Faculty of Science, Campus Miguel Delibes, 47011 Valladolid, SpainTetrahydropyrans are abundantly found in marine natural products. The interesting biological properties of these compounds and their analogues make necessary the development of convenient procedures for their synthesis. In this paper, an atom economy access to tetrahydropyrans by intramolecular acid-mediated cyclization of silylated alkenols is described. p-TsOH has shown to be an efficient reagent to yield highly substituted tetrahydropyrans. Moreover, excellent diastereoselectivities are obtained both for unsubstituted and alkylsubstituted vinylsilyl alcohols. The methodology herein developed may potentially be applied to the synthesis of marine drugs derivatives.https://www.mdpi.com/1660-3397/16/11/421tetrahydropyransacid mediated cyclizationstereoselectivemarine drugs analogues |
| spellingShingle | Carlos Díez-Poza Patricia Val Francisco J. Pulido Asunción Barbero Synthesis of Polysubstituted Tetrahydropyrans by Stereoselective Hydroalkoxylation of Silyl Alkenols: En Route to Tetrahydropyranyl Marine Analogues Marine Drugs tetrahydropyrans acid mediated cyclization stereoselective marine drugs analogues |
| title | Synthesis of Polysubstituted Tetrahydropyrans by Stereoselective Hydroalkoxylation of Silyl Alkenols: En Route to Tetrahydropyranyl Marine Analogues |
| title_full | Synthesis of Polysubstituted Tetrahydropyrans by Stereoselective Hydroalkoxylation of Silyl Alkenols: En Route to Tetrahydropyranyl Marine Analogues |
| title_fullStr | Synthesis of Polysubstituted Tetrahydropyrans by Stereoselective Hydroalkoxylation of Silyl Alkenols: En Route to Tetrahydropyranyl Marine Analogues |
| title_full_unstemmed | Synthesis of Polysubstituted Tetrahydropyrans by Stereoselective Hydroalkoxylation of Silyl Alkenols: En Route to Tetrahydropyranyl Marine Analogues |
| title_short | Synthesis of Polysubstituted Tetrahydropyrans by Stereoselective Hydroalkoxylation of Silyl Alkenols: En Route to Tetrahydropyranyl Marine Analogues |
| title_sort | synthesis of polysubstituted tetrahydropyrans by stereoselective hydroalkoxylation of silyl alkenols en route to tetrahydropyranyl marine analogues |
| topic | tetrahydropyrans acid mediated cyclization stereoselective marine drugs analogues |
| url | https://www.mdpi.com/1660-3397/16/11/421 |
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