Synthesis of Aspidospermidine

Structure of Aspidospermidine

C19H26N2

Principal investigator	Samir Z. Zard
Publication year	2006
Synthesis type	Total
Number of steps	11 (linear)
References	Org. Lett. 2006, 8, 831.

Part 1 of 1

intermediate structure

AcCl, AlCl3

CH2Cl2

98%

See the Friedel-Crafts Acylation

intermediate structure

H2, Pd/C

MeOH

91%

intermediate structure

K2CO3, MeI

Acetone

RT, 6 h, 85%

See the Williamson Ether Synthesis

intermediate structure

Li
BrCH2CO2t-Bu
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%

See the Krapcho Decarboxylation

intermediate structure

PhNHNH2

AcOH

95 °C, 8 h, 62%

See the Fischer Indole Synthesis

intermediate structure

NaBH4

MeOH

0 °C to RT, 2 h, 88%

intermediate structure

Report an error in this part