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Named reactions

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Morphine

Chemical structure of Morphine
C17H19NO3
Author Barry M. Trost
Publication year 2002
Synthesis type Formal synthesis
Number of steps 13 (linear)
References

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
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Chemical structure
Reagent structure
3-C3H3PdCl)2, Et3N
CH2Cl2
RT, 8 h, 72%

Selectivity : 94:06 er
See the Trost Asymmetic Allylation Alkylation
Chemical structure
HC(OMe)3, TsOH
MeOH
50 °C, 4 h, 100%
Chemical structure
i-Bu2AlH
PhMe
-78 °C, 60 min, 85%
Chemical structure
Reagent structure
Ph3P, DIAD
Et2O
-20 °C, 5 h

See the Mitsunobu Reaction
Chemical structure
TsOH
THF, H2O
RT, 4 h, 84% (2 steps)

98:02 er after recrystallization.
Chemical structure
Pd(OAc)2, dppp, Ag2CO3
PhMe
107 °C, 24 h, 91%

See the Heck Coupling
Chemical structure
CBr4, Ph3P
CH2Cl2
0 °C, 10 min, 91%

See the Corey-Fuchs Reaction
Chemical structure
Pd(PPh3)4, n-Bu3SnH
PhMe
RT, 20 min, 88%

See the Stille Coupling
Chemical structure
Pd(OAc)2, dppp, Ag2CO3
PhMe
107 °C, 4 h, 65%

See the Heck Coupling
The yield was 74 % brsm.
Chemical structure
SeO2, Dess-Martin Periodinane
Dioxane
75 °C to RT, 4.5 h, 58%

See the Dess-Martin Oxidation
Chemical structure
i-Bu2AlH, NH4Br, MeNH2, NaBH4
CH2Cl2, Et2O
-78 °C to RT, ON, 89%
Chemical structure
i-Pr2NLi
THF
RT, 6 h, 57%
Chemical structure

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91% (1 step)

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