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Revista de la Sociedad Química de México

versión impresa ISSN 0583-7693

Resumen

GARCIA, Cirilo; TAPIA, Josefina  y  CERVANTES, Humberto. Improved Synthesis of (20S)-3β-Acetoxy-23,24-dinorchol-5-en-22-aldehyde. Rev. Soc. Quím. Méx [online]. 2002, vol.46, n.1, pp.49-53. ISSN 0583-7693.

Commercial 3β-acetoxy-23,24-dinorchol-5-en-22-oic acid was transformed into (20S)-3β-acetoxy-23,24-dinorchol-5-en-22-aldehyde in a two-step process. The key step was reduction of the imidazolide derived from the above mentioned acid, which invariably produced the target aldehyde and 22-hydroxy-23,24-dinorchol-5-en-3β-yl acetate. In adittion to these products, the work-up of the organic material from the latter reaction, afforded pregn-5-en-3β-yl acetate along with the mixture of the former acid and its unreacted imidazolide. Oxidation of 22-hydroxy-23,24-dinorchol-5-en-3β-yl acetate with pyridinium chlorochromate and recycling of the mixture acid/imidazolide, enhances the practical value of this process. Structural analysis, based on 1H NMR spectroscopy and polarimetry of intermediate and final products, and observations on the stability of the imidazolyl derivative and aldehyde are briefly discussed.

Palabras llave : Pregn-5-ene-20-carboxaldehyde; 3-acetoxy-bisnor-5-cholenaldehyde; dinorcholenic acid; bisnorcholenic acid; steroidal imidazolid.

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