Total Synthesis of Lineaflavones A, C, D, and Analogues
The first total synthesis of lineaflavones A, C, D, and their analogues has been accomplished. The key synthetic steps include aldol/oxa-Michael/dehydration sequence reactions to assemble the tricyclic core, Claisen rearrangement and Schenck ene reaction to construct the key intermediate, and select...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-03-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/5/2373 |
| _version_ | 1797614764532170752 |
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| author | Rui Wang Yu Fu Ran Ma Hongzhen Jin Wei Zhao |
| author_facet | Rui Wang Yu Fu Ran Ma Hongzhen Jin Wei Zhao |
| author_sort | Rui Wang |
| collection | DOAJ |
| description | The first total synthesis of lineaflavones A, C, D, and their analogues has been accomplished. The key synthetic steps include aldol/oxa-Michael/dehydration sequence reactions to assemble the tricyclic core, Claisen rearrangement and Schenck ene reaction to construct the key intermediate, and selective substitution or elimination of tertiary allylic alcohol to obtain natural compounds. In addition, we also explored five new routes to synthesize fifty-three natural product analogues, which can contribute to a systematic structure–activity relationship during biological evaluation. |
| first_indexed | 2024-03-11T07:17:01Z |
| format | Article |
| id | doaj.art-cf35cae9c6d64f528f4c6182f6a535e2 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T07:17:01Z |
| publishDate | 2023-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-cf35cae9c6d64f528f4c6182f6a535e22023-11-17T08:15:45ZengMDPI AGMolecules1420-30492023-03-01285237310.3390/molecules28052373Total Synthesis of Lineaflavones A, C, D, and AnaloguesRui Wang0Yu Fu1Ran Ma2Hongzhen Jin3Wei Zhao4State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Key Laboratory of Molecular Drug Research and KLMDASR of Tianjin, Nankai University, Tongyan Road, Haihe Education Park, Tianjin 300350, ChinaState Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Key Laboratory of Molecular Drug Research and KLMDASR of Tianjin, Nankai University, Tongyan Road, Haihe Education Park, Tianjin 300350, ChinaState Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Key Laboratory of Molecular Drug Research and KLMDASR of Tianjin, Nankai University, Tongyan Road, Haihe Education Park, Tianjin 300350, ChinaState Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Key Laboratory of Molecular Drug Research and KLMDASR of Tianjin, Nankai University, Tongyan Road, Haihe Education Park, Tianjin 300350, ChinaState Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Key Laboratory of Molecular Drug Research and KLMDASR of Tianjin, Nankai University, Tongyan Road, Haihe Education Park, Tianjin 300350, ChinaThe first total synthesis of lineaflavones A, C, D, and their analogues has been accomplished. The key synthetic steps include aldol/oxa-Michael/dehydration sequence reactions to assemble the tricyclic core, Claisen rearrangement and Schenck ene reaction to construct the key intermediate, and selective substitution or elimination of tertiary allylic alcohol to obtain natural compounds. In addition, we also explored five new routes to synthesize fifty-three natural product analogues, which can contribute to a systematic structure–activity relationship during biological evaluation.https://www.mdpi.com/1420-3049/28/5/2373total synthesisflavonoidsnatural productsschenck ene reaction |
| spellingShingle | Rui Wang Yu Fu Ran Ma Hongzhen Jin Wei Zhao Total Synthesis of Lineaflavones A, C, D, and Analogues Molecules total synthesis flavonoids natural products schenck ene reaction |
| title | Total Synthesis of Lineaflavones A, C, D, and Analogues |
| title_full | Total Synthesis of Lineaflavones A, C, D, and Analogues |
| title_fullStr | Total Synthesis of Lineaflavones A, C, D, and Analogues |
| title_full_unstemmed | Total Synthesis of Lineaflavones A, C, D, and Analogues |
| title_short | Total Synthesis of Lineaflavones A, C, D, and Analogues |
| title_sort | total synthesis of lineaflavones a c d and analogues |
| topic | total synthesis flavonoids natural products schenck ene reaction |
| url | https://www.mdpi.com/1420-3049/28/5/2373 |
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