Synthesis of Minfiensine

Structure of Minfiensine

C19H22N2O

Principal investigatorLarry E. Overman
Publication year2008
Synthesis typeTotal
Number of steps 16 (linear)
References
J. Am. Chem. Soc. 2008, 130, 5368.
Part 1 of 1
intermediate structure + intermediate structure
TsOH
PhH
50 °C, 2 h, 95%
intermediate structure
TMS2NLi, MeO2CCN
THF
-78 °C, 15 min, 89%
intermediate structure
Special reagent
TMS2NNa
THF
-78 °C, 15 min, 82%
intermediate structure + intermediate structure
NaOH, (dppf)PdCl2
H2O, THF
RT, 40 min, 71%
See the Suzuki Coupling
intermediate structure
Special reagent
Cs2CO3, CsF
DMF
-78 °C, 18 min, 94%
intermediate structure
Special reagent
Pd(OAc)2, 1,2,2,6,6-Pentamethylpiperidine
PhMe
170 °C, 45 min, 87%
See the Mizoroki-Heck Reaction
"99% ee"
intermediate structure
CF3CO2H
CH2Cl2
0 °C, 30 min, 85%
intermediate structure
  1. 9-BBN
  2. H2O2 , NaOH
H2O, THF
0 to 100 °C, 2 h
intermediate structure
NMO, n-Pr4N+ RuO4-
4A MS
CH2Cl2
RT, 20 min, 63%
See the Ley-Griffith Oxidation
intermediate structure
CF3CO2H
CH2Cl2
0 °C to RT, 2.5 h
intermediate structure
Special reagent
K2CO3
MeCN
70 °C, 18 h, 65% (2 steps)
intermediate structure
K2CO3, (dppf)PdCl2.CH2Cl2
MeOH
70 °C, 1 h, 74%
intermediate structure
Special reagent
TMS2NNa
THF
-78 °C, 35 min, 86%
intermediate structure
CO, Pd(OAc)2, Ph3P
DMF, MeOH
50 °C, 3.5 h, 89%
intermediate structure
LiAlH4
THF
-20 °C, 10 min, 89%
intermediate structure
NaOH
H2O, MeOH
100 °C, 2.5 h, 95%
intermediate structure
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