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Abstract:

A new and highly efficient method for D-homo-rearrangements in the steroid field is described. The transformation is induced by the action of zinc(II) on different 17-hydroxy-20-oxopregnanes. With 17α-hydroxy-20-oxopregnanes the reaction afforded 17aα-hydroxy-17aβ-methyl-D-homo-derivatives while under the same conditions 17β-hydroxy-20-oxopregnanes gave the corresponding 17a-epimeric-D-homo-steroids. In both cases the rearrangement was stereospecif giving the corresponding products in almost quantitative yields. © 1990, The Royal Society of Chemistry. All rights reserved.

Registro:

Documento: Artículo
Título:Zinc(II)-promoted stereospecific rearrangement of 17-hydroxy-20-oxopregnane derivatives
Autor:Schor, L.; Seldes, A.M.; Gros, E.G.
Filiación:Departamento de Química Orgánica, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, Buenos Aires, 1428, Argentina
Año:1990
Número:1
Página de inicio:163
Página de fin:166
DOI: http://dx.doi.org/10.1039/P19900000163
Título revista:Journal of the Chemical Society, Perkin Transactions 1
Título revista abreviado:J. Chem. Soc. Perkin Trans. 1
ISSN:14704358
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14704358_v_n1_p163_Schor

Referencias:

  • Seldes, A.M., Gros, E.G., (1982) Steroids, 39, p. 181
  • Ruzicka, L., Meldahl, H.F., (1938) Helv. Chim. Acta, 21, p. 1760
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  • Shoppee, C.W., Prins, D.A., (1943) Helv. Chim. Acta, 26, p. 201
  • von Euw, J., Reichstein, T., (1941) Helv. Chim. Acta, 24, p. 879
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Citas:

---------- APA ----------
Schor, L., Seldes, A.M. & Gros, E.G. (1990) . Zinc(II)-promoted stereospecific rearrangement of 17-hydroxy-20-oxopregnane derivatives. Journal of the Chemical Society, Perkin Transactions 1(1), 163-166.
http://dx.doi.org/10.1039/P19900000163
---------- CHICAGO ----------
Schor, L., Seldes, A.M., Gros, E.G. "Zinc(II)-promoted stereospecific rearrangement of 17-hydroxy-20-oxopregnane derivatives" . Journal of the Chemical Society, Perkin Transactions 1, no. 1 (1990) : 163-166.
http://dx.doi.org/10.1039/P19900000163
---------- MLA ----------
Schor, L., Seldes, A.M., Gros, E.G. "Zinc(II)-promoted stereospecific rearrangement of 17-hydroxy-20-oxopregnane derivatives" . Journal of the Chemical Society, Perkin Transactions 1, no. 1, 1990, pp. 163-166.
http://dx.doi.org/10.1039/P19900000163
---------- VANCOUVER ----------
Schor, L., Seldes, A.M., Gros, E.G. Zinc(II)-promoted stereospecific rearrangement of 17-hydroxy-20-oxopregnane derivatives. J. Chem. Soc. Perkin Trans. 1. 1990(1):163-166.
http://dx.doi.org/10.1039/P19900000163