Synthesis and characterization of new podophyllotoxin derivative

Abstract:

In this paper, the synthesis and the spectroscopic study for the characterization of a new podophyllotoxin derivate is described. Podophyllotoxin 1 was isolated from the commercial resin of Podophyllum emodi W., that was used as starting material. Podophyllotoxin 1 was transformed into Podophyllotoxone 7 by an oxidation reaction. Then, 7 was treated with a mixture of t-BuOH/t-BuO-K+/H2O (95:4:5), resulting in methyl 8'-methoxy7'-(3',4',5'-trimethoxiphenyl)-8-metilnafto[4,5]dioxo-8-carboxylate(8). Both the intermediate and the product were purified and characterized by a detailed analysis from the infrared and nuclear magnetic resonance spectrums (one and two dimensional). Additionally, a possible unknown mechanism of the derivative 8 is described in the literature. In addition, the compound 8 complies with the rules established by Lipinsky and Veber.

Año de publicación:

2014

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