Efficient formal synthesis of oseltamivir phosphate (Tamiflu) with inexpensive D-ribose as the starting material.
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.
Osato
Hiroshi
H
Shionogi & Co., Ltd., 1-3, Kuise Terajima 2-chome, Amagasaki, Hyogo 660-0813, Japan.
Jones
Ian L
IL
Chen
Anqi
A
Chai
Christina L L
CL
D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000191:economics; D002384:Catalysis; D015394:Molecular Structure; D053139:Oseltamivir / Q000138:chemical synthesis* / Q000737:chemistry / Q000191:economics; D012266:Ribose / Q000737:chemistry*; D013237:Stereoisomerism
D000998:Antiviral Agents; D053139:Oseltamivir; D012266:Ribose