Synthesis of Minfiensine

C19H22N2O
Principal investigator | Larry E. Overman |
---|---|
Publication year | 2008 |
Synthesis type | Total |
Number of steps | 16 (linear) |
References |
Part 1 of 1
+
+


TsOH
PhH
50 °C, 2 h, 95%

TMS2NLi,
MeO2CCN
THF
-78 °C, 15 min, 89%


TMS2NNa
THF
-78 °C, 15 min, 82%




Cs2CO3,
CsF
DMF
-78 °C, 18 min, 94%


Pd(OAc)2,
1,2,2,6,6-Pentamethylpiperidine
PhMe
170 °C, 45 min, 87%
See the Mizoroki-Heck Reaction
"99% ee"

CF3CO2H
CH2Cl2
0 °C, 30 min, 85%

- 9-BBN
- H2O2 , NaOH
H2O, THF
0 to 100 °C, 2 h


CF3CO2H
CH2Cl2
0 °C to RT, 2.5 h


K2CO3
MeCN
70 °C, 18 h, 65% (2 steps)

K2CO3,
(dppf)PdCl2.CH2Cl2
MeOH
70 °C, 1 h, 74%


TMS2NNa
THF
-78 °C, 35 min, 86%

CO,
Pd(OAc)2,
Ph3P
DMF, MeOH
50 °C, 3.5 h, 89%

LiAlH4
THF
-20 °C, 10 min, 89%

NaOH
H2O, MeOH
100 °C, 2.5 h, 95%
