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Abstract:

The synthesis of 17α-hydroxy-3β-methoxyandrost-5-ene-17β-carbaldehyde and a highly efficient method for its D-homorearrangement is described. The transformation produced by the action of Zn IIafforded 17α-hydroxy-3β-methoxy-D-homoandrost-5-en-17a-one in a fast, stereospecific, and high-yield reaction. © Royal Society of Chemistry.

Registro:

Documento: Artículo
Título:ZnII-promoted D-homorearrangement of 17α-hydroxy-3β-methoxyandrost-5-ene-17β-carbaldehyde
Autor:Schor, L.; Gros, E.G.; Seldes, A.M.
Filiación:Departamento de Química Orgánica, Universidad de Buenos Aires, Pabellón 2, Buenos Aires, 1428, Argentina
Año:1992
Número:4
Página de inicio:453
Página de fin:454
DOI: http://dx.doi.org/10.1039/P19920000453
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_n4_p453_Schor

Referencias:

  • Wendler, N.L., (1964) Molecular Rearrangements, 2, pp. 1099-1101, 1114-1121. , P. de Mayo, Interscience, New York
  • Kirk, Q.N., Hartshorn, M.P., (1968) Steroid Reaction Mechanisms, pp. 294-301. , Elsevier, Amsterdam
  • Kirk, D.N., McHugh, C.R., (1978) J. Chem. Soc., Perkin Trans. 1, p. 173. , references therein
  • Schor, L., Seldes, A.M., Gros, E.G., (1990) J. Chem. Soc., Perkin Trans. 1, p. 163
  • Reid, J.G., Debiak-Krook, T., (1990) Tetrahedron Lett., 31, p. 3669
  • Hansen, M.M., Bartlett, P.A., Heathcock, C.H., (1987) Organometallics, 6, p. 2069

Citas:

---------- APA ----------
Schor, L., Gros, E.G. & Seldes, A.M. (1992) . ZnII-promoted D-homorearrangement of 17α-hydroxy-3β-methoxyandrost-5-ene-17β-carbaldehyde. Journal of the Chemical Society, Perkin Transactions 1(4), 453-454.
http://dx.doi.org/10.1039/P19920000453
---------- CHICAGO ----------
Schor, L., Gros, E.G., Seldes, A.M. "ZnII-promoted D-homorearrangement of 17α-hydroxy-3β-methoxyandrost-5-ene-17β-carbaldehyde" . Journal of the Chemical Society, Perkin Transactions 1, no. 4 (1992) : 453-454.
http://dx.doi.org/10.1039/P19920000453
---------- MLA ----------
Schor, L., Gros, E.G., Seldes, A.M. "ZnII-promoted D-homorearrangement of 17α-hydroxy-3β-methoxyandrost-5-ene-17β-carbaldehyde" . Journal of the Chemical Society, Perkin Transactions 1, no. 4, 1992, pp. 453-454.
http://dx.doi.org/10.1039/P19920000453
---------- VANCOUVER ----------
Schor, L., Gros, E.G., Seldes, A.M. ZnII-promoted D-homorearrangement of 17α-hydroxy-3β-methoxyandrost-5-ene-17β-carbaldehyde. J. Chem. Soc. Perkin Trans. 1. 1992(4):453-454.
http://dx.doi.org/10.1039/P19920000453