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Named reactions

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Morphine

"Dedicated to Professor Gilbert Stork."

Chemical structure of Morphine
C17H19NO3
Author Kathlyn A. Parker
Publication year 1992
Synthesis type Formal synthesis
Number of steps 17 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
Li
NH3, t-BuOH
-68 °C, 3 h, 97%

See the Birch Reduction
Chemical structure
  1. TsCl, Et3N
  2. HCl, H2O
THF
RT, 9 h, 81%
Chemical structure
MeI, K2CO3
Acetone
RT, 24 h, 96%
Chemical structure
NaBH4, CeCl3
MeOH
0 °C, 30 min, 97%

See the Luche Reduction
Chemical structure
mCPBA
CH2Cl2
0 °C, 2 h, 92%

See the Prilezhaev Reaction
Chemical structure
Ti(Oi-Pr)4
PhH
Reflux, 2 h, 85%
Chemical structure
TBSOTf, i-Pr2NEt
-78 °C, 10 min, 82%
Chemical structure + Chemical structure
n-Bu3P, DEAD
THF
0 °C, 4 h, 83%

See the Mitsunobu Reaction
Chemical structure
HF
MeCN, H2O
RT, 24 h, 98%
Chemical structure
n-Bu3SnH, AIBN
PhH
130 °C, 35 h, 35%
Chemical structure
Li, NH3
THF, t-BuOH
-78 °C, 10 min, 85%
Chemical structure
(COCl)2, Et3N
DMSO
-78 °C to RT, 2.5 h, 83%

See the Swern Oxidation
Chemical structure

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37% (5 steps)

See : Heterocycles 1977, 6, 1157; J. Med. Chem. 1977, 20, 164.
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