Synthesis of Illudinine

Structure of Illudinine

C16H17NO3

Principal investigatorRobert B. Woodward
Publication year1977
Synthesis typeTotal
Number of steps 15 (linear)
References
J. Am. Chem. Soc. 1977, 99, 8007.
Part 1 of 1
intermediate structure + intermediate structure
AlCl3
MeNO2
RT, 5.5 h, 90%
See the Friedel-Crafts Acylation
intermediate structure
H2SO4
90 °C, 4 h
See the Nazarov Cyclization Reaction
intermediate structure intermediate structure
KOt-Bu, MeI
PhH, t-BuOH
Reflux, 2 h
intermediate structure intermediate structure
HCl, Zn(Hg)
EtOH, H2O
Reflux, 25.5 h, 36% (3 steps)
See the Clemmensen Reduction
"Also isolated was the regioisomer (8 % yield)."
intermediate structure
Br2
MeNO2
RT, 60 min, 95%
intermediate structure
  1. n-BuLi
  2. B(OMe)3
  3. H2O , H2O2 , AcOH
THF
-78 °C to RT, 2 h, 56%
intermediate structure
Me2SO4, K2CO3
Acetone
Reflux, 16 h, 96%
See the Williamson Ether Synthesis
intermediate structure
  1. Br(CH2)2Br , Mg
  2. ClCO2Me
THF
RT to Reflux, 5 h, 98%
See the Grignard Reaction
intermediate structure
CrO3
AcOH
RT, 2 h, 36%
intermediate structure
NaBH4
MeOH
0 °C, 30 min, 96%
intermediate structure
TsOH
PhH
Reflux, 10 min, 100%
intermediate structure
OsO4
Et2O
RT, 15 h, 98%
intermediate structure
NaIO4
Dioxane , H2O
RT, 2 h, 100%
intermediate structure
NH4OAc
AcOH
RT, 2.5 h, 94%
intermediate structure
KOH
EtOH, H2O
RT, 20 h, 100%
intermediate structure
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