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Named reactions

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Search synthesis

Morphine

Chemical structure of Morphine
C17H19NO3
Author Catherine Guillou
Publication year 2008
Synthesis type Formal synthesis
Number of steps 18 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
Li
NH3, t-BuOH
-78 °C, 6 h, 97%

See the Birch Reduction
Chemical structure
(CH2OH)2, BF3.OEt2
Et2O
0 °C, 60 min, 81%
Chemical structure + Chemical structure
EDC, DMAP
CH2Cl2
0 °C to RT, 5 h, 80%
Chemical structure
Pd2(dba)3, Et3N
DMF
140 °C, 5 h, 60%

See the Heck Coupling
Chemical structure
Ph3C+ BF4-
CH2Cl2
RT, 2 h, 92%
Chemical structure
(PhSeO)2O
PhCl
120 °C, 8 h, 60%
Chemical structure
BnNHMe
RT, 16 h

See the Michael Addition
Chemical structure
LiAlH4
THF
0 °C to Reflux, 2 h, 77% (2 steps)
Chemical structure
CH(OMe)2NMe2
Decalin
250 °C, 2 h, 44%

See the Eschenmoser-Claisen Rearrangement
Chemical structure
Ti(Oi-Pr)4, PhSiH3
RT, 35 min
Chemical structure
TsOH
PhMe
RT, 16 h, 55% (2 steps)

See the Friedel-Crafts Alkylation
Chemical structure
ClCO2CH(Cl)CH3
DCE
0 °C to Reflux, 70 min
Chemical structure
TsCl, Et3N
CH2Cl2
RT, 16 h, 83% (2 steps)
Chemical structure
SeO2
Dioxane , t-BuOH
50 °C, 30 h
Chemical structure
Dess-Martin Periodinane
CH2Cl2
RT, 2 h

See the Dess-Martin Oxidation
Chemical structure
NaBH4
MeOH
0 °C to RT, 60 min, 28% (3 steps)
Chemical structure
Li
NH3, THF, t-BuOH
-78 °C, 8 min, 51%

The yield was 62 % brsm.
Chemical structure

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Remaining...
91% (1 step)

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