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Named reactions

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Search synthesis

Illudinine

Chemical structure of Illudinine
C16H17NO3
Author Robert B. Woodward
Publication year 1977
Synthesis type Total synthesis
Number of steps 15 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
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Chemical structure
AlCl3
MeNO2
RT, 5.5 h, 90 %

See the Friedel-Crafts Acylation
Chemical structure
H2SO4
90 °C, 4 h

See the Friedel-Crafts Alkylation
Chemical structure
+
Chemical structure
MeI, KOt-Bu
PhH, t-BuOH
Reflux, 2 h
Chemical structure
+
Chemical structure
Zn(Hg), HCl
EtOH, H2O
Reflux, 25.5 h, 36 % (3 steps)

See the Clemmensen Reduction
Also isolated was the regioisomer (8 % yield).
Chemical structure
Br2
MeNO2
RT, 60 min, 95 %
Chemical structure
  1. n-BuLi
  2. B(OMe)3
  3. H2O2, H2O, AcOH
THF
-78 °C to RT, 2 h, 56 %
Chemical structure
Me2SO4, K2CO3
Acetone
Reflux, 16 h, 96 %

See the Williamson Ether Synthesis
Chemical structure
  1. Mg, Br(CH2)2Br
  2. ClCO2Me
THF
RT to Reflux, 5 h, 98 %

See the Grignard Reaction
Chemical structure
CrO3
AcOH
RT, 2 h, 36 %
Chemical structure
NaBH4
MeOH
0 °C, 30 min, 96 %
Chemical structure
TsOH
PhH
Reflux, 10 min, 100 %
Chemical structure
OsO4
Et2O
RT, 15 h, 98 %
Chemical structure
NaIO4
Dioxane , H2O
RT, 2 h, 100 %
Chemical structure
NH4OAc
AcOH
RT, 2.5 h, 94 %
Chemical structure
KOH
EtOH, H2O
RT, 20 h, 100 %
Chemical structure

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