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Named reactions

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Search synthesis

Nupharamine

Chemical structure of Nupharamine
C15H25NO2
Author Chihiro Kibayashi
Publication year 1991
Synthesis type Total synthesis
Number of steps 17 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
CH2N2
Et2O
Chemical structure
  1. O3, NaHCO3
  2. Me2S
MeOH
-65 °C, 67% (2 steps)
Chemical structure + Chemical structure
n-BuLi
Et2O
0 °C to RT

See the Wittig Reaction
Chemical structure
I2
THF
41% (2 steps)
Chemical structure
KOH
EtOH, H2O
Chemical structure
(COCl)2
CH2Cl2
0 °C to RT
Chemical structure
NH2OH.HCl, Na2CO3
CHCl3, H2O
0 °C to RT, 77% (3 steps)
Chemical structure
n-Pr4N+ IO4-
CHCl3
0 °C, 57%

See the Diels-Alder Reaction
Also isolated was the C-4a epimer (31 %)
Chemical structure
H2, Pd/C
MeOH
96%
Chemical structure + Chemical structure
Et2O
-78 °C to RT
Chemical structure
NaBH4
AcOH
RT, 79% (2 steps)
Chemical structure
Zn
AcOH, THF
60 °C, 93%
Chemical structure
BnBr, Na2CO3
DMF
80 °C, 50%
Chemical structure
CrO3, H2SO4
Acetone, H2O
0 °C

See the Jones Oxidation
Chemical structure
CH2N2
Et2O
31% (2 steps)
Chemical structure
MeLi
Et2O
-78 °C, 91%
Chemical structure
H2, Pd(OH)2
MeOH
73%
Chemical structure

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