Synthesis of Morphine

Structure of Morphine

C17H19NO3

Principal investigatorLarry E. Overman
Publication year1993
Synthesis typeFormal
Number of steps 20 (3 parts)
References
J. Am. Chem. Soc. 1993, 115, 11028.
Part 1 of 3
intermediate structure
CBS Reagent, Catecholborane
93%
See the Itsuno-Corey Reduction
intermediate structure
PhNCO
93%
intermediate structure
OsO4, NMO
See the Upjohn Dihydroxylation
intermediate structure
TsOH
Acetone
78% (2 steps)
intermediate structure
  1. n-BuLi
  2. CuI(PPh3)2
  3. PhMe2SiLi
THF
-30 °C, 81%
intermediate structure
TsOH
MeOH
intermediate structure
NaIO4
intermediate structure
NaBH3CN, DBSNH2
82% (3 steps)
intermediate structure
Report an error in this part
Part 2 of 3
intermediate structure
  1. n-BuLi
  2. I2
intermediate structure
HCl
H2O
80% (2 steps)
intermediate structure
BnBr, K2CO3
97%
intermediate structure
Me2S=CH2
91%
See the Johnson-Corey-Chaykovsky Reaction
intermediate structure
BF3.OEt2
THF
92%
See the Semi-Pinacol Rearrangement
intermediate structure
Report an error in this part
Part 3 of 3
intermediate structure + intermediate structure
ZnI2
EtOH
60 °C, 82%
See the Hosomi-Sakurai Reaction
intermediate structure
1,2,2,6,6-Pentamethylpiperidine, Pd(CF3CO2)2(PPh3)2
PhMe
120 °C, 60%
See the Mizoroki-Heck Reaction
intermediate structure
EtSH, BF3.OEt2
79%
intermediate structure
Special reagent
Camphorsulfonic acid
CH2Cl2
0 °C, 60%
See the Prilezhaev Reaction
intermediate structure
n-Pr4N+ RuO4-, NMO
86%
See the Ley-Griffith Oxidation
intermediate structure
H2, CH2O, Pd(OH)2
80%
intermediate structure
Report an error in this part
Remaining...
37% (5 steps)
"See : Heterocycles 1977, 6, 1157; J. Med. Chem. 1977, 20, 164."
intermediate structure