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Named reactions

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Search synthesis

Luciduline

Chemical structure of Luciduline
C13H21NO
Author David A. Evans
Publication year 1972
Synthesis type Total synthesis
Number of steps 12 (linear)
References

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
IsopropenylMgBr
Selectivity : 75:25 dr
See the Grignard Reaction
No yield reported.
Chemical structure
Sealed tube
250 °C, 4 h

See the Cope Rearrangement
Chemical structure
(CH2OH)2, TsOH
THF
39 % (2 steps)

Also isolated was the C7'-epimer (26 % yield) which was equilibrated to afford the desired isomer.
Chemical structure
TsNHNH2
MeOH
RT, 3 h, 100 %
Chemical structure
MeLi
Et2O

See the Shapiro Reaction
Chemical structure
mCPBA
CHCl3
80 % (2 steps)

See the Prilezhaev Reaction
Chemical structure
NaSPh
MeOH
Reflux, 12 h, 85 %
Chemical structure
Ni (Raney)
EtOH
Reflux, 82 %
Chemical structure
TsCl
Pyr
50 °C, 10 h
Chemical structure
HCl
Acetone, H2O
50 °C, 45 min, 89 % (2 steps)
Chemical structure
MeNH2
Sealed tube
PhH
75 °C, 24 h, 94 %
Chemical structure
(CH2O)n
3-Methyl-1-butanol
Reflux, 20 h

See the Mannich Reaction
Chemical structure

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