Abstract:
A two-step synthesis of 19-functionalized 6-oxapregnanes from a 5α,6β-dihydroxypregnane is described. Deoxygenation at C-19 afforded a 6-oxapregnane, which was converted into 6-oxa-5β-pregnane-3,20-dione 7. An insight into the mechanism of formation of the key intermediate, a 5,6-secosteroid, via a hypoiodite type reaction is also given.
Registro:
Documento: |
Artículo
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Título: | Simple synthetic approach to 6-oxa steroids. Synthesis of 6-oxa-5β-pregnane-3,20-dione |
Autor: | Nicoletti, D.; Ghini, A.A.; Brachet-Cota, A.L.; Burton, G. |
Filiación: | Departamento de Química Orgánica, Universidad de Buenos Aires, Ciudad Universitaria, (1428) Buenos Aires, Argentina
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Año: | 1995
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Número: | 9
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Página de inicio: | 1089
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Página de fin: | 1093
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Título revista: | Journal of the Chemical Society, Perkin Transactions 1
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ISSN: | 14727781
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14727781_v_n9_p1089_Nicoletti |
Referencias:
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- Brachet-Cota, A.L., Burton, G., (1988) Z. Naturforsch., Teil. B, 43, p. 491
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- Hartwig, W., (1983) Tetrahedron, 39, p. 2609. , references cited therein
- Barton, D.H.R., Jang, D.O., Jaszberenyi, J.C., (1993) J. Org. Chem., 58, p. 6338
- Barton, D.H.R., Motherwell, W.B., Stange, A., (1981) Synthesis, p. 743
- De Armas, P., Concepción, J.J., Francisco, C.G., Hernandez, R., Salazar, J.A., Suarez, E., (1989) J. Chem. SOC., Perkin Trans. I, p. 405
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Citas:
---------- APA ----------
Nicoletti, D., Ghini, A.A., Brachet-Cota, A.L. & Burton, G.
(1995)
. Simple synthetic approach to 6-oxa steroids. Synthesis of 6-oxa-5β-pregnane-3,20-dione. Journal of the Chemical Society, Perkin Transactions 1(9), 1089-1093.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14727781_v_n9_p1089_Nicoletti [ ]
---------- CHICAGO ----------
Nicoletti, D., Ghini, A.A., Brachet-Cota, A.L., Burton, G.
"Simple synthetic approach to 6-oxa steroids. Synthesis of 6-oxa-5β-pregnane-3,20-dione"
. Journal of the Chemical Society, Perkin Transactions 1, no. 9
(1995) : 1089-1093.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14727781_v_n9_p1089_Nicoletti [ ]
---------- MLA ----------
Nicoletti, D., Ghini, A.A., Brachet-Cota, A.L., Burton, G.
"Simple synthetic approach to 6-oxa steroids. Synthesis of 6-oxa-5β-pregnane-3,20-dione"
. Journal of the Chemical Society, Perkin Transactions 1, no. 9, 1995, pp. 1089-1093.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14727781_v_n9_p1089_Nicoletti [ ]
---------- VANCOUVER ----------
Nicoletti, D., Ghini, A.A., Brachet-Cota, A.L., Burton, G. Simple synthetic approach to 6-oxa steroids. Synthesis of 6-oxa-5β-pregnane-3,20-dione. 1995(9):1089-1093.
Available from: https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14727781_v_n9_p1089_Nicoletti [ ]