Synthesis of Aspidospermidine

Structure of Aspidospermidine

C19H26N2

Principal investigatorSamir Z. Zard
Publication year2006
Synthesis typeTotal
Number of steps 11 (linear)
References
Part 1 of 1
intermediate structure
AcCl, AlCl3
CH2Cl2
98%
intermediate structure
H2, Pd/C
MeOH
91%
intermediate structure
K2CO3, MeI
Acetone
RT, 6 h, 85%
intermediate structure
  1. Li
  2. BrCH2CO2t-Bu
  3. H2O , HCl
NH3, t-BuOH, THF
-40 °C to RT, 6 h, 90%
See the Birch Reduction
intermediate structure
Special reagent
ClCO2i-Bu, Et3N
THF
0 °C, 2.5 h
intermediate structure
BzCl, Et3N
CH2Cl2
RT, 15 min, 67% (2 steps)
intermediate structure
n-Bu3SnH, ACCN
PhCF3
RT, 12 h, 53%
intermediate structure
9-BBN
THF
Reflux, 1 h, 93%
intermediate structure
LiCl
DMF
140 °C, 3 h, 88%
intermediate structure
PhNHNH2
AcOH
95 °C, 8 h, 62%
intermediate structure
NaBH4
MeOH
0 °C to RT, 2 h, 88%
intermediate structure