Synthesis of Aspidofractinine

Structure of Aspidofractinine

C19H24N2

Principal investigatorClaude Spino
Publication year2009
Synthesis typeTotal
Number of steps 21 (linear)
References
J. Org. Chem. 2009, 74, 6035.
Part 1 of 1
intermediate structure
  1. n-BuLi
  2. AllylBr
THF
-78 to -50 °C, 30 min, 74%
intermediate structure
TiCl4, MeOCHCl2
CH2Cl2
-78 °C, 90 min, 89%
See the Rieche Formylation
intermediate structure
Ph3P, CBr4, Et3N
CH2Cl2
-78 °C to RT, 3.5 h, 100%
See the Corey-Fuchs Reaction
intermediate structure + intermediate structure
  1. TMS2NNa
  2. n-BuLi
THF
-95 °C, 30 min
intermediate structure
Red-Al
THF
RT, 15 min, 71% (2 steps)
"Also isolated was the C1-epimer (20% yield)."
intermediate structure
Cl3CC(O)NCO
THF
0 °C, 60 min
intermediate structure
K2CO3
H2O, MeOH
0 °C to RT, 90 min, 96% (2 steps)
intermediate structure
Et3N, (CF3CO)2O, Cl3CCH2OH
CH2Cl2
0 °C to RT, 3.5 h, 87%
See the Overman Rearrangement
intermediate structure
Zn
AcOH, THF
RT, 3 h, 100%
intermediate structure
Cl(CH2)3I, K2CO3
MeCN
RT, 48 h, 77%
intermediate structure
Et3N, BrCH2COCl
CH2Cl2
0 °C, 10 min, 84%
intermediate structure
Grubbs catalyst (2nd gen.)
CH2Cl2
RT, 4 h, 86%
See the Olefin Metathesis
intermediate structure
DBU, TsNHNHTs
THF
0 °C, 92%
intermediate structure
Cu(OTf)2.3PhMe
Syringe pump
CH2Cl2
RT, 4.5 h, 70%
intermediate structure
NaI
Acetone
Reflux, 3 h
See the Finkelstein Reaction
intermediate structure
AIBN, n-Bu3SnH
PhH
Reflux, 60 min, 92% (2 steps)
intermediate structure
Na.Anthracene
DME
-70 °C, 1 min, 96%
intermediate structure
Pyr, PhSeO2H
THF
Reflux, 30 min, 61%
intermediate structure + intermediate structure
Sealed tube
PhH
90 °C, 5 h, 55%
See the Diels-Alder Reaction
intermediate structure
Ni (Raney)
i-PrOH
Reflux, 8 h, 67%
intermediate structure
LiAlH4
THF
Reflux, 2 h, 70%
intermediate structure
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