Catalytic asymmetric synthesis of cannabinoids and menthol from neral
| العنوان: | Catalytic asymmetric synthesis of cannabinoids and menthol from neral |
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| المؤلفون: | Joyce A. A. Grimm, Hui Zhou, Roberta Properzi, Markus Leutzsch, Giovanni Bistoni, Johanna Nienhaus, Benjamin List |
| المصدر: | Nature. 615:634-639 |
| بيانات النشر: | Springer Science and Business Media LLC, 2023. |
| سنة النشر: | 2023 |
| مصطلحات موضوعية: | Multidisciplinary |
| الوصف: | The selective conversion of natural or synthetic neral to (1R,6S)-trans-isopiperitenol would enable and expedite sustainable routes to menthol1,2 and cannabinoids3–5. However, this reaction has been considered impossible because its product is more reactive to the required acid catalysts than its starting material, resulting in several side products6–9. We now show that an unsymmetric, strong and confined chiral acid, a highly fluorinated imino-imidodiphosphate, catalyses this process with excellent efficiency and selectivity. Expanding the method to other α,β-unsaturated aldehydes could enable access to new cannabinoids and menthol derivatives not readily accessible previously. Mechanistic studies suggest that the confined catalyst accomplishes this reaction by binding the product in an unreactive conformation, thereby preventing its decomposition. We also show how (1R,6S)-trans-isopiperitenol can be readily converted to pharmaceutically useful cannabinoids and menthol, each in the shortest and most atom-economic routes so far. |
| تدمد: | 1476-4687 0028-0836 |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::79b9f8c35212ad6b86ae24e085bffe68 https://doi.org/10.1038/s41586-023-05747-9 |
| حقوق: | OPEN |
| رقم الأكسشن: | edsair.doi.dedup.....79b9f8c35212ad6b86ae24e085bffe68 |
| قاعدة البيانات: | OpenAIRE |
Find this article in full text from Springer Verlag. | تدمد: | 14764687 00280836 |
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