Synthesis of Oseltamivir

Structure of Oseltamivir

C16H28N2O4

Principal investigator	Barry M. Trost
Publication year	2008
Synthesis type	Total
Number of steps	9 (linear)
References	Angew. Chem. Int. Ed. 2008, 47, 3759.

Part 1 of 1

intermediate structure

Special reagent

(n3-C3H3PdCl)2, Trimethylsilylphthalimide

THF

40 °C, 8.5 h

See the Trost Asymmetic Allylation Alkylation

intermediate structure

TsOH

EtOH

Reflux, 10 h, 84% (2 steps)

See the Fischer-Speier Esterification

intermediate structure

PhSSO2Ph, TMS2NK

THF

-78 °C to RT, ON, 94%

intermediate structure

NaHCO3, mCPBA, DBU

PhMe

0 to 60 °C, 7 h, 85%

intermediate structure

TMS(CH2)2SO2NH2, PhI(OPiv)2, Rh2(esp)2, MgO

PhCl

0 °C to RT, 4 h, 86%

intermediate structure

3-Pentanol, BF3.OEt2

75 °C, 15 min, 65%

intermediate structure

DMAP, Ac2O

µW

Pyr

150 °C, 60 min, 84%

intermediate structure

n-Bu4N+ F-

THF

RT, 30 min, 95%

intermediate structure

NH2NH2

EtOH

68 °C, 10 h, 100%

intermediate structure

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