Synthesis of Nominine

C20H27NO
Principal investigator | David Y. Gin |
---|---|
Publication year | 2006 |
Synthesis type | Total |
Number of steps | 18 (3 parts) |
References |
Part 1 of 3


i-Bu2AlH
PhMe
0 °C, 30 min, 92%

Pd(PPh3)4,
Cu(CN)2
DMF
60 °C, 25 min, 85%

Part 2 of 3
+



NaN3
Acetone
RT, 38 h, 95%

AcCl
MeOH
RT, 5 min, 99%

Part 3 of 3
+



CF3CO2H
CH2Cl2
0 °C, 3 h, 93%

Sealed tube
THF
180 °C, 16 h, 20%
See the Huisgen Cycloaddition
"Also isolated was 70 % of a regioisomer which could be thermally equilibrated to the desired product."

NaBH4
EtOH
RT, 90 min

SOCl2
CH2Cl2
50 °C, 2.5 h

n-Bu3SnH,
AIBN
PhH
80 °C, 105 min, 68% (3 steps)

i-Bu2AlH
PhMe
0 °C, 100 min, 85%





SeO2,
t-BuOOH
CH2Cl2
RT, 70 min, 66%
