Abstract
The synthesis of deacetylcolchicine from colchicine is described with an overall yield of 83%. The transformation does not involve the classical tropone ring isomerization known with these products and resulting from the hydrolysis of the acetamide in acid experimental conditions.
Notes
Compound 5:1H-RMN (CDCl3, 200 MHz) 7.54 (s, 1H); 7.17 (d, J = 10.6 Hz, 1H); 6.73 (d, J = 10.6 Hz. 1H); 6.51 (s. 1H); 5.12 (dd, J = 5.8, 11.9 Hz, 1H); 3.94 (s, 3H); 3.90 (s. 3H); 3.87 (s. 3H); 3.63 (s, 3H); 2.70–2.37 (m, 3H); 2.25 (s, 3H); 2.02–1.84 (m, 1H); 1.53 (s. 9H).
Compound 6:1H-RMN (CDCl3, 200 MHz): 7.49 (s, 1H); 7.23 (d, J = 10.7 Hz, 1H); 6.79 (d. J = 10.7 Hz, 1H); 6.51 (s. 1H); 5.06 (d. J = 7.6 Hz, 1H); 4.42–4.35 (m, 1H); 3.97 (s, 3H); 3.90 (s, 3H); 3.87 (s, 3H); 3.62 (s, 3H); 2.51–2.16 (m, 3H); 1.72–1.63 (m, 1H); 1.33 (s, 9H).