1287204-69-6Relevant articles and documents
Enantioselective synthesis of oseltamivir phosphate
Raghavan, Sadagopan,Babu, Vaddela Sudheer
, p. 2044 - 2050 (2011/04/17)
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.