Synthesis of Oseltamivir

Structure of Oseltamivir

C16H28N2O4

Principal investigatorTohru Fukuyama
Publication year2007
Synthesis typeTotal
Number of steps 14 (linear)
References
Angew. Chem. Int. Ed. 2007, 46, 5734.
Part 1 of 1
intermediate structure
NaBH4, ClCO2Bn
MeOH
-47 to 0 °C, 50 min
intermediate structure
Special reagent
Acrolein
H2O, MeCN
RT, 14 h
See the Diels-Alder Reaction
intermediate structure
NaH2PO4, NaClO2, 2-Methyl-2-butene
H2O, t-BuOH
0 °C to RT, 70 min
See the Pinnick-Lindgren Oxidation
intermediate structure
Br2, NaHCO3
CH2Cl2, H2O
RT, 26% (4 steps)
intermediate structure
H2, Pd/C, Boc2O
1 atm
EtOH, THF
RT, 2 h, 92%
intermediate structure
RuO2, NaIO4
DCE, H2O
80 °C, 3.5 h, 86%
intermediate structure
NH3
t-BuOH, THF
0 °C, 2.5 h, 95%
intermediate structure
Et3N, MsCl
CH2Cl2
RT, 40 min, 91%
intermediate structure
PhI(OAc)2, AllylOH
4 Å MS
DCE
60 °C, 11 h, 88%
See the Hofmann Rearrangement
intermediate structure
NaOEt
EtOH
0 °C, 87%
intermediate structure
BF3.OEt2, 3-Pentanol
-20 °C, 50 min, 62%
intermediate structure
CF3CO2H
CH2Cl2
0 °C to RT, 3 h
intermediate structure
Ac2O
Pyr
RT, 60 min, 72% (2 steps)
intermediate structure
Pd/C, Ph3P, Dimethylbarbituric acid
EtOH
Reflux, 60 min, 76%
intermediate structure
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