Synthesis of Oseltamivir

Structure of Oseltamivir

C16H28N2O4

Principal investigator	Elias J. Corey
Publication year	2006
Synthesis type	Total
Number of steps	12 (linear)
References	J. Am. Chem. Soc. 2006, 128, 6310.

Part 1 of 1

intermediate structure

+

intermediate structure

Special reagent

RT, 30 h, 97%

See the Diels-Alder Reaction

intermediate structure

NH3

CF3CH2OH

40 °C, 5 h, 100%

intermediate structure

TMSOTf, Et3N

Pentane

0 °C to RT, 2 h

intermediate structure

I2

Et2O, THF

0 °C, 3 h, 84% (2 steps)

intermediate structure

Boc2O, Et3N, DMAP

CH2Cl2

RT, 4 h, 99%

intermediate structure

DBU

THF

Reflux, 12 h, 96%

intermediate structure

NBS, AIBN

CCl4

Reflux, 2 h, 95%

See the Wohl-Ziegler Reaction

intermediate structure

Cs2CO3

EtOH

RT, 25 min, 100%

intermediate structure

N-Bromoacetamide, SnBr4

MeCN

-40 °C, 4 h, 75%

intermediate structure

n-Bu4N+ Br-, TMS2NK

DME

-20 °C, 10 min, 82%

intermediate structure

Cu(OTf)2, 3-Pentanol

0 °C, 12 h, 61%

intermediate structure

H3PO4

EtOH

intermediate structure

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