Synthesis of Oseltamivir

Structure of Oseltamivir

C16H28N2O4

Principal investigatorUlrich Zutter
Publication year2008
Synthesis typeTotal
Number of steps 13 (linear)
References
J. Org. Chem. 2008, 73, 4895.
Part 1 of 1
intermediate structure + intermediate structure
KOt-Bu
DMSO
50 °C, 5 h
See the Williamson Ether Synthesis
intermediate structure
NBS
DMF
0 °C to RT, 19 h, 90% (2 steps)
intermediate structure
CO, KOAc, Pd(OAc)2, dppp
10 atm
EtOH
110 °C, 15 h, 95%
intermediate structure
H2, Ru/Al2O3
100 atm
EtOAc
60 °C, 24 h, 82%
intermediate structure
TMSCl, NaI
H2O, MeCN
40 °C, 15 h, 97%
intermediate structure
Pig liver esterase
Buffer (pH = 8)
35 °C, 46 h, 98%
intermediate structure
Et3N, (PhO)2P(O)N3
CH2Cl2
40 °C, 16 h, 78%
See the Curtius Rearrangement
intermediate structure
DMAP, NaH, Boc2O
PhMe
RT to Reflux, 5.5 h
intermediate structure
Pyr, Tf2O
CH2Cl2
-10 °C, 3 h, 85% (2 steps)
intermediate structure
NaN3
Acetone, H2O
RT, 15 h, 78%
intermediate structure
H2, Co (Raney)
1 atm
RT, 20 h
intermediate structure
Ac2O, Et3N
EtOAc
RT, 60 min
intermediate structure
HBr
AcOH, EtOAc
RT, 20 h, 83% (3 steps)
intermediate structure
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