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.
| Original language | English |
|---|---|
| Article number | ss-2016-z0587-op |
| Pages (from-to) | 424-428 |
| Number of pages | 5 |
| Journal | Synthesis (Germany) |
| Volume | 49 |
| Issue number | 2 |
| DOIs | |
| Publication status | Published - 2017 Jan 18 |
Keywords
- Tamiflu
- continuous flow
- organocatalysis
- time economy
- total synthesis
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry