Synthesis of Oseltamivir

Structure of Oseltamivir

C16H28N2O4

Principal investigatorBarry M. Trost
Publication year2008
Synthesis typeTotal
Number of steps 9 (linear)
References
Part 1 of 1
intermediate structure
(n3-C3H3PdCl)2, Trimethylsilylphthalimide
THF
40 °C, 8.5 h
intermediate structure
TsOH
EtOH
Reflux, 10 h, 84% (2 steps)
intermediate structure
TMS2NK, PhSSO2Ph
THF
-78 °C to RT, ON, 94%
intermediate structure
DBU, mCPBA, NaHCO3
PhMe
0 to 60 °C, 7 h, 85%
intermediate structure
MgO, Rh2(esp)2, PhI(OPiv)2, TMS(CH2)2SO2NH2
PhCl
0 °C to RT, 4 h, 86%
intermediate structure
BF3.OEt2, 3-Pentanol
75 °C, 15 min, 65%
intermediate structure
Ac2O, DMAP
Pyr
150 °C, 60 min, 84%
intermediate structure
n-Bu4N+ F-
THF
RT, 30 min, 95%
intermediate structure
NH2NH2
EtOH
68 °C, 10 h, 100%
intermediate structure