Synthesis of Oseltamivir

Structure of Oseltamivir

C16H28N2O4

Principal investigatorMasakatsu Shibasaki
Publication year2007
Synthesis typeTotal
Number of steps 14 (linear)
References
Org. Lett. 2007, 9, 259.
Part 1 of 1
intermediate structure
Special reagent
TMSN3, Y(Oi-Pr)3, 2,6-Dimethylphenol
EtCN
RT, 12 h, 94%
"Cristallized to >99:01 er (72 % yield)."
intermediate structure
DMAP, NaOH, Boc2O
H2O, MeCN
RT, 2 h, 98%
intermediate structure
K2CO3, I2, KI
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
2,6-Lutidine, AcSH
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%
See the Dess-Martin Oxidation
intermediate structure
(EtO)2P(O)CN, LiCN
THF
-20 °C, 7 h
intermediate structure
Sealed tube
PhMe
140 °C, 40 min, 78% (2 steps)
intermediate structure
  1. DEAD , p-NO2BzOH , Ph3P
  2. LiOH , H2O
THF
-20 °C, 3 h, 80%
See the Mitsunobu Reaction
intermediate structure
DEAD, Ph3P
THF
-20 °C, 75 min, 66%
See the Mitsunobu Reaction
intermediate structure
BF3.OEt2, 3-Pentanol
5 Å MS
-20 °C, 75 min, 56%
intermediate structure
HCl
EtOH, H2O
RT, 31.5 h, 60%
See the Pinner Reaction
intermediate structure
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