Synthesis of Oseltamivir

Structure of Oseltamivir

C16H28N2O4

Principal investigatorElias J. Corey
Publication year2006
Synthesis typeTotal
Number of steps 12 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
RT, 30 h, 97%
intermediate structure
NH3
CF3CH2OH
40 °C, 5 h, 100%
intermediate structure
Et3N, TMSOTf
Pentane
0 °C to RT, 2 h
intermediate structure
I2
Et2O, THF
0 °C, 3 h, 84% (2 steps)
intermediate structure
DMAP, Et3N, Boc2O
CH2Cl2
RT, 4 h, 99%
intermediate structure
DBU
THF
Reflux, 12 h, 96%
intermediate structure
AIBN, NBS
CCl4
Reflux, 2 h, 95%
intermediate structure
Cs2CO3
EtOH
RT, 25 min, 100%
intermediate structure
SnBr4, N-Bromoacetamide
MeCN
-40 °C, 4 h, 75%
intermediate structure
TMS2NK, n-Bu4N+ Br-
DME
-20 °C, 10 min, 82%
intermediate structure
3-Pentanol, Cu(OTf)2
0 °C, 12 h, 61%
intermediate structure
H3PO4
EtOH
intermediate structure