Synthesis of Nupharamine

C15H25NO2
Principal investigator | Chihiro Kibayashi |
---|---|
Publication year | 1991 |
Synthesis type | Total |
Number of steps | 17 (linear) |
References |
Part 1 of 1
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CH2N2
Et2O

- O3 , NaHCO3
- Me2S
MeOH
-65 °C, 67% (2 steps)



I2
hν
THF
41% (2 steps)

KOH
EtOH, H2O

(COCl)2
CH2Cl2
0 °C to RT

Na2CO3,
NH2OH.HCl
CHCl3, H2O
0 °C to RT, 77% (3 steps)

n-Pr4N+ IO4-
CHCl3
0 °C, 57%
See the Diels-Alder Reaction
"Also isolated was the C-4a epimer (31 %)"

Pd/C,
H2
MeOH
96%


Et2O
-78 °C to RT

NaBH4
AcOH
RT, 79% (2 steps)

Zn
AcOH, THF
60 °C, 93%

BnBr,
Na2CO3
DMF
80 °C, 50%


CH2N2
Et2O
31% (2 steps)

MeLi
Et2O
-78 °C, 91%

H2,
Pd(OH)2
MeOH
73%
