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Named reactions

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Search synthesis

Tacamonine

Chemical structure of Tacamonine
C19H22N2O
Author Mauri Lounasmaa
Publication year 1995
Synthesis type Total synthesis
Number of steps 12 (linear)
References

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
+
Chemical structure
100 °C, 90 min, 96 %
Chemical structure
H2, Pd/C, Et3N
MeOH
RT, 15 h, 94 %
Chemical structure
HCl
MeOH
RT, 30 h, 85 %

See the Pictet-Spengler Reaction
Chemical structure
CF3CO2H
79 %
Chemical structure
LiAlH4
THF
60 °C, 45 min, 92 %
Chemical structure
TsCl
Pyr
-20 °C, 80 %
Chemical structure
NaCN
DMF
60 °C, 95 %
Chemical structure
NaOH
H2O
Chemical structure
POCl3
90 % (2 steps)
Chemical structure
mCPBA
Chemical structure
(CF3CO)2O
CH2Cl2
RT, 52 % (2 steps)

See the Polonovski-Potier Reaction
Chemical structure
NaBH4
AcOH, MeOH
50 %

Also isolated was the C20-epimer (25 % yield).
Chemical structure

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