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Named reactions

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Search synthesis

Morphine

Chemical structure of Morphine
C17H19NO3
Author Larry E. Overman
Publication year 1993
Synthesis type Formal synthesis
Number of steps 24 (3 parts)
Reference

Browse hundreds of other total syntheses.

Part 1 of 3
Chemical structure
CBS Reagent, Catecholborane
93%

Selectivity : >98:02 er
See the Corey-Itsuno Reaction
Chemical structure
PhNCO
93%
Chemical structure
OsO4, NMO
See the Upjohn Dihydroxylation
Chemical structure
TsOH
Acetone
78% (2 steps)
Chemical structure
  1. n-BuLi
  2. CuI(PPh3)2
  3. PhMe2SiLi
THF
-30 °C, 81%
Chemical structure
TsOH
MeOH
Chemical structure
NaIO4
Chemical structure
DBSNH2, NaBH3CN
82% (3 steps)
Chemical structure

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Part 2 of 3
Chemical structure
  1. n-BuLi
  2. I2
Chemical structure
HCl
H2O
80% (2 steps)
Chemical structure
BnBr, K2CO3
97%
Chemical structure
Chemical structure
BF3.OEt2
THF
92%

See the Semi-Pinacol Rearrangement
Chemical structure

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Part 3 of 3
Chemical structure
+
Chemical structure
ZnI2
EtOH
60 °C, 82%

Selectivity : >95:05 dr
See the Hosomi-Sakurai Reaction
Chemical structure
Pd(CF3CO2)2(PPh3)2, 1,2,2,6,6-Pentamethylpiperidine
PhMe
120 °C, 60%

See the Heck Coupling
Chemical structure
BF3.OEt2, EtSH
79%
Chemical structure
Reagent structure
Camphorsulfonic acid
CH2Cl2
0 °C, 60%

See the Prilezhaev Reaction
Chemical structure
n-Pr4N+ RuO4-, NMO
86%

See the Ley-Griffith Oxidation
Chemical structure
H2, Pd(OH)2, CH2O
80%
Chemical structure

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Remaining...
37% (5 steps)

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