Efficient formal synthesis of oseltamivir phosphate (Tamiflu) with inexpensive D-ribose as the starting material

Organic Letters
Hiroshi OsatoChristina L L Chai

Abstract

An efficient formal synthesis of oseltamivir phosphate (Tamiflu) has been achieved in 12 steps with use of the inexpensive and highly abundant D-ribose as the starting material. This concise alternative route does not utilize protecting groups and features the introduction of 3-pentylidene ketal as the latent 3-pentyl ether, the use of a highly efficient RCM reaction to form the Tamiflu skeleton, and selective functional group manipulations.

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