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
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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
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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
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Volumen: | 39
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Número: | 2
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Página de inicio: | 181
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Página de fin: | 190
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DOI: |
http://dx.doi.org/10.1016/0039-128X(82)90085-X |
Título revista: | Steroids
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Título revista abreviado: | Steroids
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ISSN: | 0039128X
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CODEN: | STEDA
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CAS: | Acetic Acids; ethyl bromoacetate, 105-36-2; Hydrocarbons, Brominated; Pregnenes
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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