Synthesis of Tacamonine

Structure of Tacamonine

C19H22N2O

Principal investigatorMauri Lounasmaa
Publication year1995
Synthesis typeTotal
Number of steps 12 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
100 °C, 90 min, 96%
intermediate structure
Et3N, H2, Pd/C
MeOH
RT, 15 h, 94%
intermediate structure
HCl
MeOH
RT, 30 h, 85%
intermediate structure
CF3CO2H
79%
intermediate structure
LiAlH4
THF
60 °C, 45 min, 92%
intermediate structure
TsCl
Pyr
-20 °C, , 80%
intermediate structure
NaCN
DMF
60 °C, , 95%
intermediate structure
NaOH
H2O
intermediate structure
POCl3
90% (2 steps)
intermediate structure
mCPBA
intermediate structure
(CF3CO)2O
CH2Cl2
RT, , 52% (2 steps)
intermediate structure
NaBH4
AcOH, MeOH
50%
"Also isolated was the C20-epimer (25 % yield)."
intermediate structure