Synthesis of Oseltamivir

C16H28N2O4
Principal investigator | Tohru Fukuyama |
---|---|
Publication year | 2007 |
Synthesis type | Total |
Number of steps | 14 (linear) |
References |
Part 1 of 1

NaBH4,
ClCO2Bn
MeOH
-47 to 0 °C, 50 min


NaH2PO4,
NaClO2,
2-Methyl-2-butene
H2O, t-BuOH
0 °C to RT, 70 min
See the Pinnick-Lindgren Oxidation

Br2,
NaHCO3
CH2Cl2, H2O
RT, 26% (4 steps)

H2,
Pd/C,
Boc2O
1 atm
EtOH, THF
RT, 2 h, 92%

RuO2,
NaIO4
DCE, H2O
80 °C, 3.5 h, 86%

NH3
t-BuOH, THF
0 °C, 2.5 h, 95%

Et3N,
MsCl
CH2Cl2
RT, 40 min, 91%


NaOEt
EtOH
0 °C, 87%

BF3.OEt2,
3-Pentanol
-20 °C, 50 min, 62%

CF3CO2H
CH2Cl2
0 °C to RT, 3 h

Ac2O
Pyr
RT, 60 min, 72% (2 steps)

Pd/C,
Ph3P,
Dimethylbarbituric acid
EtOH
Reflux, 60 min, 76%
