Synthesis of Oseltamivir

Structure of Oseltamivir

C16H28N2O4

Principal investigatorMasakatsu Shibasaki
Publication year2007
Synthesis typeTotal
Number of steps 14 (linear)
References
Part 1 of 1
intermediate structure
TMSN3, Y(Oi-Pr)3, 2,6-Dimethylphenol
EtCN
RT, 12 h, 94%
"Cristallized to >99:01 er (72 % yield)."
intermediate structure
Boc2O, NaOH, DMAP
MeCN, H2O
RT, 2 h, 98%
intermediate structure
I2, KI, K2CO3
CHCl3
60 °C, 14 h
intermediate structure
DBU
CHCl3
4 °C to RT, 4 h, 85% (2 steps)
intermediate structure
Boc2O, Et3N, DMAP
CH2Cl2
4 °C to RT, 2 h, 99%
intermediate structure
AcSH, 2,6-Lutidine
CHCl3
60 °C, 19 h, 83%
intermediate structure
Cs2CO3
n-BuOH
RT, 16 h, 86%
intermediate structure
Dess-Martin Periodinane
CH2Cl2
4 °C to RT, 25 min, 90%
intermediate structure
(EtO)2P(O)CN, LiCN
THF
-20 °C, 7 h
intermediate structure
PhMe
140 °C, 40 min, 78% (2 steps)
intermediate structure
  1. p-NO2BzOH
  2. Ph3P
  3. DEAD
  4. LiOH
  5. H2O
THF
-20 °C, 3 h, 80%
intermediate structure
Ph3P, DEAD
THF
-20 °C, 75 min, 66%
intermediate structure
3-Pentanol, BF3.OEt2
-20 °C, 75 min, 56%
intermediate structure
HCl
EtOH, H2O
RT, 31.5 h, 60%
See the Pinner Reaction
intermediate structure