Synthesis of Colchicine

Structure of Colchicine

C22H25NO6

Principal investigatorMartin G. Banwell
Publication year1996
Synthesis typeTotal
Number of steps 15 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
NaOH
MeOH
RT, 48 h, 96%
intermediate structure
H2, Pd/C
EtOAc
RT, 10 h, 96%
intermediate structure
NaBH4
THF
RT, 90 min, 96%
intermediate structure
Pb(OAc)4
CH2Cl2
RT, 60 min, 100%
intermediate structure
CF3CO2H
PhH, THF
0 °C, 60 min, 42%
intermediate structure
BnBr, K2CO3
MeCN
82 °C, 4 h, 88%
intermediate structure
NMO, n-Pr4N+ RuO4-
CH2Cl2
RT, 43 h, 98%
intermediate structure
CBS Reagent
THF
RT, 6 h, 88%
intermediate structure
H2, Pd/C
EtOAc
RT, 9 h, 99%
intermediate structure
Tl(NO3)3
MeOH
-20 °C, 30 min, 83%
intermediate structure
Me3SO+ I-, NaH
DMSO
RT, 7 h, 54%
intermediate structure
CF3CO2H
CH2Cl2
RT, 3 h, 48%
intermediate structure
DIAD, Ph3P, Zn(N3)2.2Pyr
THF
RT, 38 h, 30%
intermediate structure
Ph3P
H2O, THF
RT, 2.5 d
intermediate structure
Ac2O
Pyr
RT, 15 min, 60% (2 steps)
intermediate structure