A Revised Protecting Group Strategy Enables a Divergent Synthesis of Prenylated Isoflavones from Psoralea corylifolia
Three bioactive prenylated isoflavone natural products were synthesized for the first time, using a combination of Pd-catalyzed Suzuki–Miyaura coupling for installing the B-ring, microwave-promoted Claisen rearrangement of allyl ethers, and Ru-catalyzed olefin cross me tathesis for obtaining the pre...
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| Format: | Article |
| Language: | English |
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Synthesis
2025
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| Online Access: | http://hdl.handle.net/20.500.12493/2918 |
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| author | Gliszczinskia Sarah von Chamier Sperlicha Eric Kellinga Alexandra Kwesiga George Schmidt Bernd |
| author_facet | Gliszczinskia Sarah von Chamier Sperlicha Eric Kellinga Alexandra Kwesiga George Schmidt Bernd |
| author_sort | Gliszczinskia Sarah von Chamier |
| collection | KAB-DR |
| description | Three bioactive prenylated isoflavone natural products were synthesized for the first time, using a combination of Pd-catalyzed Suzuki–Miyaura coupling for installing the B-ring, microwave-promoted Claisen rearrangement of allyl ethers, and Ru-catalyzed olefin cross me tathesis for obtaining the prenyl substituents. Careful consideration of the protecting group strategy turned out to be vital for the success of these total syntheses. |
| format | Article |
| id | oai:idr.kab.ac.ug:20.500.12493-2918 |
| institution | KAB-DR |
| language | English |
| publishDate | 2025 |
| publisher | Synthesis |
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| spelling | oai:idr.kab.ac.ug:20.500.12493-29182025-06-14T00:00:19Z A Revised Protecting Group Strategy Enables a Divergent Synthesis of Prenylated Isoflavones from Psoralea corylifolia Gliszczinskia Sarah von Chamier Sperlicha Eric Kellinga Alexandra Kwesiga George Schmidt Bernd isoflavones Suzuki coupling Claisen rearrangement ole fin metathesis protecting groups Three bioactive prenylated isoflavone natural products were synthesized for the first time, using a combination of Pd-catalyzed Suzuki–Miyaura coupling for installing the B-ring, microwave-promoted Claisen rearrangement of allyl ethers, and Ru-catalyzed olefin cross me tathesis for obtaining the prenyl substituents. Careful consideration of the protecting group strategy turned out to be vital for the success of these total syntheses. 2025-06-13T09:36:35Z 2025-06-13T09:36:35Z 2025 Article von Chamier Gliszczinski, S., Sperlich, E., Kelling, A., Kwesiga, G., & Schmidt, B. (2025). A Revised Protecting Group Strategy Enables a Divergent Synthesis of Prenylated Isoflavones from Psoralea corylifolia. Synthesis, 57(11), 1833-1847. 10.1055/a-2501-4796; http://hdl.handle.net/20.500.12493/2918 en Attribution-NonCommercial-NoDerivs 3.0 United States http://creativecommons.org/licenses/by-nc-nd/3.0/us/ application/pdf Synthesis |
| spellingShingle | isoflavones Suzuki coupling Claisen rearrangement ole fin metathesis protecting groups Gliszczinskia Sarah von Chamier Sperlicha Eric Kellinga Alexandra Kwesiga George Schmidt Bernd A Revised Protecting Group Strategy Enables a Divergent Synthesis of Prenylated Isoflavones from Psoralea corylifolia |
| title | A Revised Protecting Group Strategy Enables a Divergent Synthesis of Prenylated Isoflavones from Psoralea corylifolia |
| title_full | A Revised Protecting Group Strategy Enables a Divergent Synthesis of Prenylated Isoflavones from Psoralea corylifolia |
| title_fullStr | A Revised Protecting Group Strategy Enables a Divergent Synthesis of Prenylated Isoflavones from Psoralea corylifolia |
| title_full_unstemmed | A Revised Protecting Group Strategy Enables a Divergent Synthesis of Prenylated Isoflavones from Psoralea corylifolia |
| title_short | A Revised Protecting Group Strategy Enables a Divergent Synthesis of Prenylated Isoflavones from Psoralea corylifolia |
| title_sort | revised protecting group strategy enables a divergent synthesis of prenylated isoflavones from psoralea corylifolia |
| topic | isoflavones Suzuki coupling Claisen rearrangement ole fin metathesis protecting groups |
| url | http://hdl.handle.net/20.500.12493/2918 |
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