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Named reactions

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Aspidofractinine

Chemical structure of Aspidofractinine
C19H24N2
Author Claude Spino
Publication year 2009
Synthesis type Total synthesis
Number of steps 21 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
  1. n-BuLi
  2. AllylBr
THF
-78 to -50 °C, 30 min, 74%
Chemical structure
TiCl4, MeOCHCl2
CH2Cl2
-78 °C, 90 min, 89%

See the Rieche Formylation
Chemical structure
CBr4, Ph3P, Et3N
CH2Cl2
-78 °C to RT, 3.5 h, 100%

See the Corey-Fuchs Reaction
Chemical structure + Chemical structure
  1. TMS2NNa
  2. n-BuLi
THF
-95 °C, 30 min
Chemical structure
Red-Al
THF
RT, 15 min, 71% (2 steps)

Also isolated was the C1-epimer (20% yield).
Chemical structure
Cl3CC(O)NCO
THF
0 °C, 60 min
Chemical structure
K2CO3
MeOH, H2O
0 °C to RT, 90 min, 96% (2 steps)
Chemical structure
(CF3CO)2O, Et3N, Cl3CCH2OH
CH2Cl2
0 °C to RT, 3.5 h, 87%

See the Overman Rearrangement
Chemical structure
Zn
THF, AcOH
RT, 3 h, 100%
Chemical structure
Cl(CH2)3I, K2CO3
MeCN
RT, 48 h, 77%
Chemical structure
BrCH2COCl, Et3N
CH2Cl2
0 °C, 10 min, 84%
Chemical structure
Grubbs catalyst (2nd gen.)
CH2Cl2
RT, 4 h, 86%

See the Olefin Metathesis
Chemical structure
TsNHNHTs, DBU
THF
0 °C, 92%
Chemical structure
Cu(OTf)2.3PhMe
Syringe pump
CH2Cl2
RT, 4.5 h, 70%
Chemical structure
NaI
Acetone
Reflux, 3 h

See the Finkelstein Reaction
Chemical structure
n-Bu3SnH, AIBN
PhH
Reflux, 60 min, 92% (2 steps)
Chemical structure
Na.Anthracene
DME
-70 °C, 1 min, 96%
Chemical structure
PhSeO2H, Pyr
THF
Reflux, 30 min, 61%
Chemical structure + Chemical structure
Sealed tube
PhH
90 °C, 5 h, 55%

See the Diels-Alder Reaction
Chemical structure
Ni (Raney)
i-PrOH
Reflux, 8 h, 67%
Chemical structure
LiAlH4
THF
Reflux, 2 h, 70%
Chemical structure

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