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Named reactions

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Search synthesis

Magallanesine

Chemical structure of Magallanesine
C21H17NO6
Author Takushi Kurihara
Publication year 1994
Synthesis type Partial synthesis
Number of steps 13 (linear)
References

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
H2, Pd/C
4 atm
MeOH, AcOH
RT, 3 h, 99 %

The starting material is obtained in 5 steps from piperonal, see: Chem. Pharm. Bull. 1987, 35, 479.
Chemical structure
LiAlH4
THF
RT, 10 min, 93 %
Chemical structure
SOCl2
CH2Cl2
Reflux, 2 h, 100 %
Chemical structure
NaOMe
MeOH
Reflux, 90 min, 72 %
Chemical structure
H2O2
CHCl3, MeOH, H2O
RT, 15 h
Chemical structure
THF
Reflux, 60 min, 64 % (2 steps)

See the Meisenheimer Rearrangement
Chemical structure
H2, Pd/C
1 atm
MeOH
RT, 15 h, 100 %
Chemical structure
+
Chemical structure
NaOH
DME, H2O
RT, 10 min, 94 %

See the Schotten-Baumann Reaction
Chemical structure
Dess-Martin Periodinane
CH2Cl2
RT, 30 min, 95 %

See the Dess-Martin Oxidation
Chemical structure
  1. TMS2NNa
  2. (PhS)2
THF, HMPA
-78 °C to RT, 90 min
Chemical structure
mCPBA, NaHCO3
CH2Cl2
RT, 10 min
Chemical structure
PhMe
Reflux, 60 min, 67 % (3 steps)
Chemical structure
Pd(OAc)2, Ph3P, TlOAc
DMF
130 °C, 24 h, 93 %

See the Heck Coupling
Chemical structure

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