One-Pot Synthesis of Hydroxylated Alkaloids from Sugars via a Pictet–Spengler-Type Reaction
An efficient and convenient strategy has been successfully developed for the preparation of novel hydroxylated alkaloid derivatives (also called fused multicyclic iminosugars) from <i>p</i>-toluenesulfonylated sugars through a Pictet–Spengler-type mechanism. This method is highly stereos...
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| Format: | Article |
| Language: | English |
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MDPI AG
2024-12-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/29/23/5709 |
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| author | Likai Zhou Na Ma Jilai Wu Weilin Yang Lijing Feng Song Xie Lili Wang Hua Chen |
| author_facet | Likai Zhou Na Ma Jilai Wu Weilin Yang Lijing Feng Song Xie Lili Wang Hua Chen |
| author_sort | Likai Zhou |
| collection | DOAJ |
| description | An efficient and convenient strategy has been successfully developed for the preparation of novel hydroxylated alkaloid derivatives (also called fused multicyclic iminosugars) from <i>p</i>-toluenesulfonylated sugars through a Pictet–Spengler-type mechanism. This method is highly stereoselective, does not require metal catalysts, and capable of conducting gram level reactions (with a 53% yield). Some of such iminosugars had an intermediate antiproliferative effect on HCT116 tumor cells. |
| format | Article |
| id | doaj-art-6f6de4fe38b14b2b89911f82eb50faae |
| institution | Kabale University |
| issn | 1420-3049 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-6f6de4fe38b14b2b89911f82eb50faae2024-12-13T16:28:47ZengMDPI AGMolecules1420-30492024-12-012923570910.3390/molecules29235709One-Pot Synthesis of Hydroxylated Alkaloids from Sugars via a Pictet–Spengler-Type ReactionLikai Zhou0Na Ma1Jilai Wu2Weilin Yang3Lijing Feng4Song Xie5Lili Wang6Hua Chen7Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Material Science, Hebei University, Baoding 071002, ChinaAsset Management Co., Ltd., Hebei University, Baoding 071002, ChinaComprehensive Experimental Center, Hebei University, Baoding 071002, ChinaKey Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Material Science, Hebei University, Baoding 071002, ChinaKey Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Material Science, Hebei University, Baoding 071002, ChinaKey Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Material Science, Hebei University, Baoding 071002, ChinaFunctional Polymer Materials R&D and Engineering Application Technology Innovation Center of Hebei, College of Chemical Engineering and Biotechnology, Xingtai University, Xingtai 054001, ChinaKey Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Material Science, Hebei University, Baoding 071002, ChinaAn efficient and convenient strategy has been successfully developed for the preparation of novel hydroxylated alkaloid derivatives (also called fused multicyclic iminosugars) from <i>p</i>-toluenesulfonylated sugars through a Pictet–Spengler-type mechanism. This method is highly stereoselective, does not require metal catalysts, and capable of conducting gram level reactions (with a 53% yield). Some of such iminosugars had an intermediate antiproliferative effect on HCT116 tumor cells.https://www.mdpi.com/1420-3049/29/23/5709hydroxylated alkaloidsfused multicyclic iminosugarsPictet–Spengler reactionantitumor activity |
| spellingShingle | Likai Zhou Na Ma Jilai Wu Weilin Yang Lijing Feng Song Xie Lili Wang Hua Chen One-Pot Synthesis of Hydroxylated Alkaloids from Sugars via a Pictet–Spengler-Type Reaction Molecules hydroxylated alkaloids fused multicyclic iminosugars Pictet–Spengler reaction antitumor activity |
| title | One-Pot Synthesis of Hydroxylated Alkaloids from Sugars via a Pictet–Spengler-Type Reaction |
| title_full | One-Pot Synthesis of Hydroxylated Alkaloids from Sugars via a Pictet–Spengler-Type Reaction |
| title_fullStr | One-Pot Synthesis of Hydroxylated Alkaloids from Sugars via a Pictet–Spengler-Type Reaction |
| title_full_unstemmed | One-Pot Synthesis of Hydroxylated Alkaloids from Sugars via a Pictet–Spengler-Type Reaction |
| title_short | One-Pot Synthesis of Hydroxylated Alkaloids from Sugars via a Pictet–Spengler-Type Reaction |
| title_sort | one pot synthesis of hydroxylated alkaloids from sugars via a pictet spengler type reaction |
| topic | hydroxylated alkaloids fused multicyclic iminosugars Pictet–Spengler reaction antitumor activity |
| url | https://www.mdpi.com/1420-3049/29/23/5709 |
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