Synthesis of Nominine

Structure of Nominine

C20H27NO

Principal investigatorDavid Y. Gin
Publication year2006
Synthesis typeTotal
Number of steps 18 (3 parts)
References
Part 1 of 3
intermediate structure
  1. Tf2O
  2. Et2AlCN
  3. n-Bu4N+ Ph3SiF2-
PhH
0 °C to RT, 19.5 h, 81%
intermediate structure
i-Bu2AlH
PhMe
0 °C, 30 min, 92%
intermediate structure
Pd(PPh3)4, Cu(CN)2
DMF
60 °C, 25 min, 85%
intermediate structure
Part 2 of 3
intermediate structure + intermediate structure
t-BuLi
Et2O
-23 °C, 4.5 h, 52%
intermediate structure
NaN3
Acetone
RT, 38 h, 95%
intermediate structure
AcCl
MeOH
RT, 5 min, 99%
intermediate structure
Part 3 of 3
intermediate structure + intermediate structure
n-Bu3P, NaBH(OAc)3
CH2Cl2
RT, 17 h, 79%
See the Wittig Reaction
intermediate structure
CF3CO2H
CH2Cl2
0 °C, 3 h, 93%
intermediate structure
THF
180 °C, 16 h, 20%
"Also isolated was 70 % of a regioisomer which could be thermally equilibrated to the desired product."
intermediate structure
NaBH4
EtOH
RT, 90 min
intermediate structure
SOCl2
CH2Cl2
50 °C, 2.5 h
intermediate structure
AIBN, n-Bu3SnH
PhH
80 °C, 105 min, 68% (3 steps)
intermediate structure
i-Bu2AlH
PhMe
0 °C, 100 min, 85%
intermediate structure
n-BuLi, Ph3P+CH3 Br-
THF
RT, 95 min, 96%
See the Wittig Reaction
intermediate structure
Na
i-PrOH, NH3, THF
-78 °C, 4 h, 97%
See the Birch Reduction
"Acidic quench."
intermediate structure
Pyrrolidine
MeOH
60 °C, 4.5 h, 78%
intermediate structure
n-BuLi, Ph3P+CH3 Br-
THF
70 °C, 15 h, 77%
See the Wittig Reaction
intermediate structure
SeO2, t-BuOOH
CH2Cl2
RT, 70 min, 66%
intermediate structure