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Named reactions

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Nominine

Chemical structure of Nominine
C20H27NO
Author David Y. Gin
Publication year 2006
Synthesis type Total synthesis
Number of steps 18 (3 parts)
Reference

Browse hundreds of other total syntheses.

Part 1 of 3
Chemical structure
  1. Et2AlCN
  2. n-Bu4N+ Ph3SiF2-
  3. Tf2O
PhH
0 °C to RT, 19.5 h, 81%

See the Michael Addition
Chemical structure
i-Bu2AlH
PhMe
0 °C, 30 min, 92%
Chemical structure
Cu(CN)2, Pd(PPh3)4
DMF
60 °C, 25 min, 85%
Chemical structure

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Part 2 of 3
Chemical structure
+
Chemical structure
t-BuLi
Et2O
-23 °C, 4.5 h, 52%

See the Weinreb Ketone Synthesis
Chemical structure
NaN3
Acetone
RT, 38 h, 95%
Chemical structure
AcCl
MeOH
RT, 5 min, 99%
Chemical structure

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Part 3 of 3
Chemical structure
+
Chemical structure
n-Bu3P, NaBH(OAc)3
CH2Cl2
RT, 17 h, 79%

See the Wittig Reaction
Chemical structure
CF3CO2H
CH2Cl2
0 °C, 3 h, 93%
Chemical structure
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.
Chemical structure
NaBH4
EtOH
RT, 90 min
Chemical structure
SOCl2
CH2Cl2
50 °C, 2.5 h
Chemical structure
n-Bu3SnH, AIBN
PhH
80 °C, 105 min, 68% (3 steps)
Chemical structure
i-Bu2AlH
PhMe
0 °C, 100 min, 85%
Chemical structure
Ph3P+CH3 Br-, n-BuLi
THF
RT, 95 min, 96%

See the Wittig Reaction
Chemical structure
Na
NH3, i-PrOH, THF
-78 °C, 4 h, 97%

See the Birch Reduction
Acidic quench.
Chemical structure
Pyrrolidine
MeOH
60 °C, 4.5 h, 78%

See the Diels-Alder Reaction
Chemical structure
Ph3P+CH3 Br-, n-BuLi
THF
70 °C, 15 h, 77%

See the Wittig Reaction
Chemical structure
SeO2, t-BuOOH
CH2Cl2
RT, 70 min, 66%
Chemical structure

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