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Named reactions

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Morphine

"Dedicated to Professor Wilhelm Fleischhacker on the occasion of his 65th birthday."

Chemical structure of Morphine
C17H19NO3
Author Johann Mulzer
Publication year 1996
Synthesis type Formal synthesis
Number of steps 20 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
HCO2Me, NaOMe
PhH
95%

See the Claisen Condensation
Chemical structure + Chemical structure
Et3N
MeOH

See the Robinson Annulation
Chemical structure
KOH
Dioxane , H2O
77% (2 steps)

The enantiomers were resolved on a preparative scale by chromatography on cellulose triacetate.
Chemical structure
  1. Vinyl2CuMgCl
  2. TMSCl, Et3N
THF
-78 °C to RT

See the Michael Addition
Chemical structure
NBS
THF
-78 °C, 63% (2 steps)

Also isolated was the CX-epimer (21 % yield).
Chemical structure
DMF
140 °C, 100%
Chemical structure
TMSCl, (CH2OH)2
CH2Cl2
92%
Chemical structure
  1. BH3.Me2S
  2. H2O2, NaOH, H2O
THF
70%
Chemical structure
Ni (Raney), KOH
MeOH
98%
Chemical structure
Reagent structure
PhSO2NHMe, n-Bu3P
81%

See the Mitsunobu Reaction
Chemical structure
NBS, Bz2O2
CCl4
Reflux, 65%
Chemical structure
Li, NH3
THF, t-BuOH
79%
Chemical structure
HCl
H2O
90 °C, 95%
Chemical structure

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Remaining...
39% (7 steps)

See : J. Med, Chem, 1976, 19, 1171; J. Med. Chem. 1977, 20, 164; J. Am. Chem. Soc. 1953, 75, 4340.
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