Synthesis of Oseltamivir

Structure of Oseltamivir

C16H28N2O4

Principal investigator	Yujiro Hayashi
Publication year	2009
Synthesis type	Total
Number of steps	8 (linear)
References	Angew. Chem. Int. Ed. 2009, 48, 1304.

Part 1 of 1

intermediate structure

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intermediate structure

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intermediate structure

Special reagent

ClCH2CO2H

CH2Cl2

0 °C to RT, 3.5 h

See the Michael Addition

intermediate structure

p-MePhSH

EtOH

-15 °C, 36 h, 70% (2 steps)

See the Michael Addition

intermediate structure

CF3CO2H

CH2Cl2

RT, 2 h

intermediate structure

DMF, (COCl)2

CH2Cl2

0 °C to RT, 60 min

intermediate structure

NaN3

Acetone, H2O

0 °C, 20 min

intermediate structure

Ac2O

AcOH

RT, 49 h

See the Curtius Rearrangement

intermediate structure

Zn, TMSCl

EtOH

70 °C, 2 h

intermediate structure

K2CO3, NH3

EtOH

0 °C to RT, 6 h, 82% (6 steps)

intermediate structure

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