Synthesis of Nupharamine

Structure of Nupharamine

C15H25NO2

Principal investigatorChihiro Kibayashi
Publication year1991
Synthesis typeTotal
Number of steps 17 (linear)
References
Tetrahedron Lett. 1991, 32, 4325.
Part 1 of 1
intermediate structure
CH2N2
Et2O
intermediate structure
  1. O3 , NaHCO3
  2. Me2S
MeOH
-65 °C, 67% (2 steps)
intermediate structure + intermediate structure
n-BuLi
Et2O
0 °C to RT
See the Wittig Reaction
intermediate structure
I2
hν
THF
41% (2 steps)
intermediate structure
KOH
EtOH, H2O
intermediate structure
(COCl)2
CH2Cl2
0 °C to RT
intermediate structure
Na2CO3, NH2OH.HCl
CHCl3, H2O
0 °C to RT, 77% (3 steps)
intermediate structure
n-Pr4N+ IO4-
CHCl3
0 °C, 57%
See the Diels-Alder Reaction
"Also isolated was the C-4a epimer (31 %)"
intermediate structure
Pd/C, H2
MeOH
96%
intermediate structure + intermediate structure
Et2O
-78 °C to RT
intermediate structure
NaBH4
AcOH
RT, 79% (2 steps)
intermediate structure
Zn
AcOH, THF
60 °C, 93%
intermediate structure
BnBr, Na2CO3
DMF
80 °C, 50%
intermediate structure
CrO3, H2SO4
Acetone, H2O
0 °C
See the Jones Oxidation
intermediate structure
CH2N2
Et2O
31% (2 steps)
intermediate structure
MeLi
Et2O
-78 °C, 91%
intermediate structure
H2, Pd(OH)2
MeOH
73%
intermediate structure
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