Multistep Continuous-Flow Synthesis of (–)-Oseltamivir
Abstract A continuous-flow synthesis of (–)-oseltamivir composed of five flow units was accomplished. In each unit, the following reactions proceed efficiently: (1) a diphenylprolinol silyl ether mediated Michael reaction, (2) a domino reaction of Michael and intermolecular Horner–Wadsworth–Emmons r...
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| Veröffentlicht in: | Synthesis (Stuttgart) 2016-11, Vol.49 (2), p.424-428 |
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| Hauptverfasser: | , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
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| Zusammenfassung: | Abstract
A continuous-flow synthesis of (–)-oseltamivir composed of five flow units was accomplished. In each unit, the following reactions proceed efficiently: (1) a diphenylprolinol silyl ether mediated Michael reaction, (2) a domino reaction of Michael and intermolecular Horner–Wadsworth–Emmons reactions, (3) protonation, (4) epimerization, and (5) reduction of a nitro group to an amine. (–)-Oseltamivir was obtained in 13% total yield through a single flow with a residence time of 310 minutes. |
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| ISSN: | 0039-7881 1437-210X |
| DOI: | 10.1055/s-2016-0036-1588899 |