Synthesis of Morphine
C17H19NO3
Principal investigator | Larry E. Overman |
---|---|
Publication year | 1993 |
Synthesis type | Formal |
Number of steps | 20 (3 parts) |
References |
Part 1 of 3
PhNCO
93%
TsOH
Acetone
78% (2 steps)
- n-BuLi
- CuI(PPh3)2
- PhMe2SiLi
THF
-30 °C, 81%
TsOH
MeOH
NaIO4
NaBH3CN,
DBSNH2
82% (3 steps)
Part 2 of 3
- n-BuLi
- I2
HCl
H2O
80% (2 steps)
BnBr,
K2CO3
97%
Part 3 of 3
+
EtSH,
BF3.OEt2
79%
H2,
CH2O,
Pd(OH)2
80%
Remaining...
37% (5 steps)
"See : Heterocycles 1977, 6, 1157; J. Med. Chem. 1977, 20, 164."