| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5221606 | Tetrahedron | 2011 | 7 Pages |
The key steps in the enantioselective synthesis of Tamiflu include an asymmetric Diels-Alder reaction, Mitsunobu inversion using Fukuyama modified Weinreb reagent, carbamate directed epoxidation. Epoxide opening with trimethylsilyl azide furnished a 3:1 mixture of regioisomers that converged to afford the same aziridine. Attempted preparation of the unsaturated ester regioselectively using 2-iodoxybenzoic acid (IBX) following Nicolaou's protocol failed. The unsaturated ester was prepared by phenylselenylation followed by selenoxide elimination.
Graphical abstractAn enantioselective synthesis of Tamiflu is disclosed. The key steps include an asymmetric Diels-Alder reaction, Mitsunobu inversion using Fukuyama modified Weinreb reagent and carbamate directed epoxidation. Download full-size image
