Synthesis of Aspidofractinine

C19H24N2
Principal investigator | Claude Spino |
---|---|
Publication year | 2009 |
Synthesis type | Total |
Number of steps | 21 (linear) |
References |
Part 1 of 1
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- n-BuLi
- AllylBr
THF
-78 to -50 °C, 30 min, 74%




- TMS2NNa
- n-BuLi
THF
-95 °C, 30 min

Red-Al
THF
RT, 15 min, 71% (2 steps)
"Also isolated was the C1-epimer (20% yield)."

Cl3CC(O)NCO
THF
0 °C, 60 min

K2CO3
H2O, MeOH
0 °C to RT, 90 min, 96% (2 steps)


Zn
AcOH, THF
RT, 3 h, 100%

Cl(CH2)3I,
K2CO3
MeCN
RT, 48 h, 77%

Et3N,
BrCH2COCl
CH2Cl2
0 °C, 10 min, 84%


DBU,
TsNHNHTs
THF
0 °C, 92%

Cu(OTf)2.3PhMe
Syringe pump
CH2Cl2
RT, 4.5 h, 70%


AIBN,
n-Bu3SnH
PhH
Reflux, 60 min, 92% (2 steps)

Na.Anthracene
DME
-70 °C, 1 min, 96%

Pyr,
PhSeO2H
THF
Reflux, 30 min, 61%



Ni (Raney)
i-PrOH
Reflux, 8 h, 67%

LiAlH4
THF
Reflux, 2 h, 70%
