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Abstract:

Reformatsky reaction of 3β, 21-diacyloxy- and 3β-methoxy-21-acyloxy-5-pregnen-20-one with ethyl bromoacetate yields, through an intramolecular 1,2-acyl migration, 3β, 20ξ-diacyloxy- and 3β-methoxy-20ξ-acyloxy-14α-card-5-enolide respectively. The 20ξ-acyloxy-14α-card-5-enolides were converted into the respective 20ξ-hydroxy-14α-card-5-enolides and the 14α-carda-5,20(22)-dienolides. Experimental support to the proposed intramolecular 1,2-acyl migration is provided by the use of labelled compounds. © 1982.

Registro:

Documento: Artículo
Título:Acyl migration in the Reformatsky reaction of 21-acyloxy-5-pregnen-20-one derivatives with ethyl bromoacetate
Autor:Seldes, A.M.; Gros, E.G.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellon 2, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Palabras clave:21 acyloxypregn 5 en 20 one; bromoacetic acid ethyl ester; theoretical study; Acetic Acids; Acylation; Hydrocarbons, Brominated; Pregnenes; Support, Non-U.S. Gov't
Año:1982
Volumen:39
Número:2
Página de inicio:181
Página de fin:190
DOI: http://dx.doi.org/10.1016/0039-128X(82)90085-X
Título revista:Steroids
Título revista abreviado:Steroids
ISSN:0039128X
CODEN:STEDA
CAS:Acetic Acids; ethyl bromoacetate, 105-36-2; Hydrocarbons, Brominated; Pregnenes
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v39_n2_p181_Seldes

Referencias:

  • Seldes, Anding, Gros, (1980) Steroids, 36, p. 575
  • Doerschuk, (1952) J.Am.Chem.Soc., 74, p. 4202
  • van Tamelen, (1951) J.Am.Chem.Soc., 73, p. 5773
  • Bonner, (1959) J.Org.Chem., 24, p. 1388
  • Steiger, Reichstein, Desoxy-cortico-steron (21-Oxy-progesteron) aus ?5-3-Oxy-�tio-cholens�ure (1937) Helvetica Chimica Acta, 20, p. 1164
  • Oka, Hara, (1978) J.Org.Chem., 43, p. 4408
  • Seldes, Gros, (1979) J.Steroid Biochem., 11, p. 1573
  • Ruzicka, Reichstein, Furst, �ber Steroide und Sexualhormone. (66. Mitteilung). Herstellung von Lactonen vom Typus der Digitalis-Genine (1941) Helvetica Chimica Acta, 24, p. 76
  • Baron, Cointet, Bauduin, Pietrasanta, Pucci, (1979) Bull.Soc.Chim.France II, p. 369
  • Frankenfeld, Werner, (1969) J. Org. Chem., 34, p. 3689
  • Pettit, Herald, Yardley, (1970) J.Org.Chem., 35, p. 1389
  • Butenandt, Grosse, Über den Ersatz der 3-ständigen Hydroxylgruppe im Pregnenolon und Androstendiol durch Chlor (1937) Berichte der deutschen chemischen Gesellschaft (A and B Series), 70, p. 1446
  • Huffman, Sadler, (1953) J.Org.Chem., 18, p. 919

Citas:

---------- APA ----------
Seldes, A.M. & Gros, E.G. (1982) . Acyl migration in the Reformatsky reaction of 21-acyloxy-5-pregnen-20-one derivatives with ethyl bromoacetate. Steroids, 39(2), 181-190.
http://dx.doi.org/10.1016/0039-128X(82)90085-X
---------- CHICAGO ----------
Seldes, A.M., Gros, E.G. "Acyl migration in the Reformatsky reaction of 21-acyloxy-5-pregnen-20-one derivatives with ethyl bromoacetate" . Steroids 39, no. 2 (1982) : 181-190.
http://dx.doi.org/10.1016/0039-128X(82)90085-X
---------- MLA ----------
Seldes, A.M., Gros, E.G. "Acyl migration in the Reformatsky reaction of 21-acyloxy-5-pregnen-20-one derivatives with ethyl bromoacetate" . Steroids, vol. 39, no. 2, 1982, pp. 181-190.
http://dx.doi.org/10.1016/0039-128X(82)90085-X
---------- VANCOUVER ----------
Seldes, A.M., Gros, E.G. Acyl migration in the Reformatsky reaction of 21-acyloxy-5-pregnen-20-one derivatives with ethyl bromoacetate. Steroids. 1982;39(2):181-190.
http://dx.doi.org/10.1016/0039-128X(82)90085-X