Synthesis of Colchicine

Structure of Colchicine

C22H25NO6

Principal investigatorDavid A. Evans
Publication year1981
Synthesis typeFormal
Number of steps 12 (linear)
References
Part 1 of 1
intermediate structure
Me2SO4, KOH
MeOH, H2O
Reflux, 90 min, 90%
intermediate structure
Pt (Anode), KOH
MeOH
0 °C, 25 h
intermediate structure
(CO2H)2
THF, H2O
RT, 12 h, 65% (2 steps)
intermediate structure
Me3SO+ I-, NaH
DMSO
0 °C, 3 h, 91%
intermediate structure + intermediate structure
i-Pr2NLi, (CO2H)2
THF, THF
-70 °C, 2 h
See the Aldol Addition
"Mixture of isomers."
intermediate structure
(CO2H)2
THF, H2O
RT, 5 h, 95% (2 steps)
"Mixture of isomers."
intermediate structure
CF3CO2H
Reflux, 35 min, 92%
intermediate structure
DDQ
PhH
Reflux, 18 h, 54%
intermediate structure
NaOMe
MeOH, H2O
75 °C, 45 min, 85%
intermediate structure
(PhO)2P(O)N3, Et3N
t-BuOH
Reflux, 17 h, 54%
intermediate structure
HCl
H2O
110 °C, 90 min, 72%
intermediate structure
Remaining...
(2 steps)
"See : Helv. Chim. Acta 1957, 40, 193; Helv. Chim. Acta 1946, 29, 246."
intermediate structure