Synthesis of Morphine
C17H19NO3
Principal investigator | Barry M. Trost |
---|---|
Publication year | 2002 |
Synthesis type | Formal |
Number of steps | 13 (linear) |
References |
Part 1 of 1
+
HC(OMe)3,
TsOH
MeOH
50 °C, 4 h, 100%
i-Bu2AlH
PhMe
-78 °C, 60 min, 85%
TsOH
H2O, THF
RT, 4 h, 84% (2 steps)
"98:02 er after recrystallization."
Pd(OAc)2,
dppp,
Ag2CO3
PhMe
107 °C, 4 h, 65%
See the Mizoroki-Heck Reaction
"The yield was 74 % brsm."
i-Bu2AlH,
NaBH4,
MeNH2,
NH4Br
CH2Cl2, Et2O
-78 °C to RT, ON, 89%
i-Pr2NLi
hν
THF
RT, 6 h, 57%
Remaining...
91% (1 step)
"See : J. Med. Chem. 1977, 20, 164."