Synthesis of Illudinine

C16H17NO3
Principal investigator | Robert B. Woodward |
---|---|
Publication year | 1977 |
Synthesis type | Total |
Number of steps | 15 (linear) |
References |
Part 1 of 1
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KOt-Bu,
MeI
PhH, t-BuOH
Reflux, 2 h


HCl,
Zn(Hg)
EtOH, H2O
Reflux, 25.5 h, 36% (3 steps)
See the Clemmensen Reduction
"Also isolated was the regioisomer (8 % yield)."

Br2
MeNO2
RT, 60 min, 95%

- n-BuLi
- B(OMe)3
- H2O , H2O2 , AcOH
THF
-78 °C to RT, 2 h, 56%



CrO3
AcOH
RT, 2 h, 36%

NaBH4
MeOH
0 °C, 30 min, 96%

TsOH
PhH
Reflux, 10 min, 100%

OsO4
Et2O
RT, 15 h, 98%

NaIO4
Dioxane , H2O
RT, 2 h, 100%

NH4OAc
AcOH
RT, 2.5 h, 94%

KOH
EtOH, H2O
RT, 20 h, 100%
