Synthesis of Oseltamivir

C16H28N2O4
Principal investigator | Ulrich Zutter |
---|---|
Publication year | 2008 |
Synthesis type | Total |
Number of steps | 13 (linear) |
References |
Part 1 of 1
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NBS
DMF
0 °C to RT, 19 h, 90% (2 steps)

CO,
KOAc,
Pd(OAc)2,
dppp
10 atm
EtOH
110 °C, 15 h, 95%

H2,
Ru/Al2O3
100 atm
EtOAc
60 °C, 24 h, 82%

TMSCl,
NaI
H2O, MeCN
40 °C, 15 h, 97%

Pig liver esterase
Buffer (pH = 8)
35 °C, 46 h, 98%


DMAP,
NaH,
Boc2O
PhMe
RT to Reflux, 5.5 h

Pyr,
Tf2O
CH2Cl2
-10 °C, 3 h, 85% (2 steps)

NaN3
Acetone, H2O
RT, 15 h, 78%

H2,
Co (Raney)
1 atm
RT, 20 h

Ac2O,
Et3N
EtOAc
RT, 60 min

HBr
AcOH, EtOAc
RT, 20 h, 83% (3 steps)
