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
- Turner, R.B., (1953) J. Am. Chem. Soc., 75, p. 3484
- Fukushima, D.K., Dobriner, S., Heffler, M.S., Kritchevsky, T.H., Herling, F., Roberts, G., (1955) J. Am. Chem. Soc., 77, p. 6585
- Kirk, D.N., Mudd, A., (1975) J. Chem. Soc., Perkin Trans. 1, p. 1450
- Mills, J.S., Ringold, H.J., Djerassi, C., (1958) J. Am. Chem. Soc., 80, p. 6118
- Defaye, G., Fétizon, M., (1969) Bull. Soc. Chim. Fr., p. 1632
- Oliveto, E.P., Gerold, C., Rausser, R., Hershberg, E.B., (1955) J. Am. Chem. Soc., 77, p. 3564
- Dvolaitzky, M., Giroud, A.M., Jacques, J., (1963) Bull. Soc. Chim. Fr., p. 62
- 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
- Stavely, H.E., (1939) J. Am. Chem. Soc., 61, p. 79
- Hegner, P., Reichstein, T., (1941) Helv. Chim. Acta, 24, p. 828
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