Synthesis of Luciduline

Structure of Luciduline

C13H21NO

Principal investigatorDavid A. Evans
Publication year1972
Synthesis typeTotal
Number of steps 12 (linear)
References
Part 1 of 1
intermediate structure
IsopropenylMgBr
"No yield reported."
intermediate structure
250 °C, 4 h
intermediate structure
(CH2OH)2, TsOH
THF
39% (2 steps)
"Also isolated was the C7'-epimer (26 % yield) which was equilibrated to afford the desired isomer."
intermediate structure
TsNHNH2
MeOH
RT, 3 h, 100%
intermediate structure
MeLi
Et2O
intermediate structure
mCPBA
CHCl3
80% (2 steps)
intermediate structure
NaSPh
MeOH
Reflux, 12 h, 85%
intermediate structure
Ni (Raney)
EtOH
Reflux, , 82%
intermediate structure
TsCl
Pyr
50 °C, 10 h
intermediate structure
HCl
Acetone, H2O
50 °C, 45 min, 89% (2 steps)
intermediate structure
MeNH2
PhH
75 °C, 24 h, 94%
intermediate structure
(CH2O)n
3-Methyl-1-butanol
Reflux, 20 h
intermediate structure