Synthesis of Colchicine

C22H25NO6

Principal investigator	David A. Evans
Publication year	1981
Synthesis type	Formal
Number of steps	12 (linear)
References	J. Am. Chem. Soc. 1981, 103, 5813.

Part 1 of 1

KOH, Me2SO4

H2O, MeOH

Reflux, 90 min, 90%

See the Williamson Ether Synthesis

Pt (Anode), KOH

4.0 V

MeOH

0 °C, 25 h

(CO2H)2

H2O, THF

RT, 12 h, 65% (2 steps)

NaH, Me3SO+ I-

DMSO

0 °C, 3 h, 91%

See the Johnson-Corey-Chaykovsky Reaction

i-Pr2NLi, 																	
																						(CO2H)2

																	THF															

								-70 °C, 								2 h								
							
								See the Aldol Addition
							
								"Mixture of isomers."

(CO2H)2

H2O, THF

RT, 5 h, 95% (2 steps)

"Mixture of isomers."

CF3CO2H

Reflux, 35 min, 92%

DDQ

PhH

Reflux, 18 h, 54%

NaOMe

H2O, MeOH

75 °C, 45 min, 85%

Et3N, (PhO)2P(O)N3

t-BuOH

Reflux, 17 h, 54%

See the Curtius Rearrangement

HCl

H2O

110 °C, 90 min, 72%

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Remaining...

(2 steps)

"See : Helv. Chim. Acta 1957, 40, 193; Helv. Chim. Acta 1946, 29, 246."