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Named reactions

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Search synthesis

Morphine

Chemical structure of Morphine
C17H19NO3
Author James D. White
Publication year 1999
Synthesis type Formal synthesis
Number of steps 28 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
+
Chemical structure
NaOMe
MeOH
Reflux, 6 h, 68%

See the Stobbe Condensation
Chemical structure
Reagent structure
H2, [RhCl(COD)]2
1 atm
THF, MeOH
RT, 10 h, 100%

Selectivity : 97:03 er
Chemical structure
Br2
AcOH
RT, 10 min, 92%
Chemical structure
P2O5
MsOH
RT, 10 h, 75%

See the Friedel-Crafts Acylation
Chemical structure
H2, Pd(OH)2, NaHCO3
1 atm
MeOH
RT, 45 min, 99%
Chemical structure
LiOH
THF, H2O
RT, 12 h, 100%
Chemical structure
KH, HCO2Me
THF
RT, 8 h

See the Claisen Condensation
Chemical structure + Chemical structure
Et3N
CH2Cl2
RT, 12 h

See the Michael Addition
Chemical structure
NaOH
THF, H2O
RT, 10 h, 70% (3 steps)

See the Aldol Condensation
Chemical structure
CH2N2
EtOAc, Et2O
RT, 90%
Chemical structure
Br2, NaHCO3
CHCl3
0 °C, 90 min, 70%
Chemical structure
DBU
PhH
68 °C, 4 h, 90%
Chemical structure
NaBH4
CH2Cl2, i-PrOH
RT, 12 h, 99%
Chemical structure
H2, Pd/C, NaHCO3
1 atm
MeOH
RT, 24 h, 75%
Chemical structure
CH2(OMe)2, P2O5
CHCl3
RT, 4 h, 86%
Chemical structure
LiOH
THF, H2O
RT, 20 h, 100%
Chemical structure
(COCl)2, CH2N2
PhH, Et2O
RT, 19 h, 63%
Chemical structure
Rh2(CH3CONH)4
CH2Cl2
RT, 60 min, 65%
Chemical structure
NH2OH.HCl, NaOAc
MeOH
RT, 6 h, 90%
Chemical structure
BsCl, Et3N, DMAP
CH2Cl2
RT, 60 min
Chemical structure
AcOH
RT, 60 min, 69% (2 steps)

See the Beckmann Rearrangement
Chemical structure
NaH, MeI
PhH
Reflux, 5 h, 95%
Chemical structure
HBr
MeCN, H2O
RT, 2 h, 95%
Chemical structure
Dess-Martin Periodinane
CHCl3
RT, 60 min, 96%

See the Dess-Martin Oxidation
Chemical structure
KOt-Bu, PhSeCl
THF, t-BuOH
0 °C to RT, 90 min
Chemical structure
NaIO4
THF, H2O
RT, 30 h, 64% (2 steps)
Chemical structure
LiAlH4
THF
Reflux, 6 h, 70%
Chemical structure

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Remaining...
91% (1 step)

See : J. Med. Chem. 1977, 20, 164.
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