Synthesis of Tacamonine

Structure of Tacamonine

C19H22N2O

Principal investigatorMauri Lounasmaa
Publication year1995
Synthesis typeTotal
Number of steps 12 (linear)
References
Tetrahedron Lett. 1995, 36, 7141. Helv. Chim. Acta 1994, 77, 709.
Part 1 of 1
intermediate structure + intermediate structure
100 °C, 90 min, 96%
intermediate structure
Et3N, Pd/C, H2
MeOH
RT, 15 h, 94%
intermediate structure
HCl
MeOH
RT, 30 h, 85%
See the Pictet-Spengler Reaction
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)
See the Polonovski-Potier Reaction
intermediate structure
NaBH4
AcOH, MeOH
50%
"Also isolated was the C20-epimer (25 % yield)."
intermediate structure
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