Synthesis of Nupharamine

Structure of Nupharamine

C15H25NO2

Principal investigatorFranklin A. Davis
Publication year2006
Synthesis typeFormal
Number of steps 8 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
Ti(OEt)4
CH2Cl2
RT, 5 h, 92%
intermediate structure
2-Butanone, TMS2NK
Et2O
-78 °C, 90 min, 84%
intermediate structure
CF3CO2H
MeOH
0 °C, 2 h
intermediate structure + intermediate structure
MgSO4
CH2Cl2
RT, 2 h, 86% (2 steps)
intermediate structure
TsOH
PhH
60 °C, 4 h, 74%
intermediate structure
(CH2SH)2, BF3.OEt2
CH2Cl2
0 °C to RT, 2 h, 93%
intermediate structure
Ni (Raney)
EtOH
Reflux, 2 h, 78%
intermediate structure
Remaining...
(3 steps)
"See: J. Org. Chem. 1999, 64, 3736."
intermediate structure