Synthesis of Colchicine

Structure of Colchicine

C22H25NO6

Principal investigator	Martin G. Banwell
Publication year	1996
Synthesis type	Total
Number of steps	15 (linear)
References	Pure Appl. Chem. 1996, 68, 539.

Part 1 of 1

intermediate structure

+

intermediate structure

NaOH

MeOH

RT, 48 h, 96%

See the Claisen-Schmidt Condensation

intermediate structure

H2, Pd/C

EtOAc

RT, 10 h, 96%

intermediate structure

NaBH4

THF

RT, 90 min, 96%

intermediate structure

Pb(OAc)4

3 Å MS

CH2Cl2

RT, 60 min, 100%

intermediate structure

CF3CO2H

3 Å MS

PhH, THF

0 °C, 60 min, 42%

intermediate structure

BnBr, K2CO3

MeCN

82 °C, 4 h, 88%

intermediate structure

NMO, n-Pr4N+ RuO4-

4 Å MS

CH2Cl2

RT, 43 h, 98%

See the Ley-Griffith Oxidation

intermediate structure

CBS Reagent

THF

RT, 6 h, 88%

See the Itsuno-Corey Reduction

intermediate structure

Pd/C, H2

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%

See the Johnson-Corey-Chaykovsky Reaction

intermediate structure

CF3CO2H

CH2Cl2

RT, 3 h, 48%

intermediate structure

DIAD, Ph3P, Zn(N3)2.2Pyr

THF

RT, 38 h, 30%

See the Mitsunobu Reaction

intermediate structure

Ph3P

H2O, THF

RT, 2.5 d

See the Staudinger Reaction

intermediate structure

Ac2O

Pyr

RT, 15 min, 60% (2 steps)

intermediate structure

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