Artículo
Nicoletti, D.; Ghini, A.A.; Baggio, R.F.; Garland, M.T.; Burton, G. "Rearrangement of 18-iodo- and 20-iodopregnanes mediated by iodosyl derivatives" (2001) Journal of the Chemical Society. Perkin Transactions 1. 1(13):1511-1517
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Abstract:
Conversion of 20-acetoxy-18-iodopregn-4-en-3-one 1 to the 18-iodosyl derivative by MCPBA resulted in a Wagner–Meerwein-type rearrangement with regioselective migration of the C13–C17 bond to give, in high yield, an abeo-pregnane in which C-18 was incorporated into ring D. The rearranged steroid was epoxidized in situ yielding a mixture of β and α 13,14-epoxides (3 and 4) which were characterized spectroscopically and by X-ray crystallography. When (20R)-20-iodopregn-4-en-3-one 9 was used as substrate, regioselective migration of the C16–C17 bond gave the D-homoandrostane with incorporation of C-20 into ring D in up to 95% yield. The 20S epimer 9 however, gave a mixture of substitution and rearrangement products. The crystal structures of the deacetylated β-epoxide 3 (5), the methanolysis product of α-epoxide 4 (7) and 20-iodopregnanes 9 and 9 are reported. © 2001 The Royal Society of Chemistry.
Registro:
| Documento: | Artículo |
| Título: | Rearrangement of 18-iodo- and 20-iodopregnanes mediated by iodosyl derivatives |
| Autor: | Nicoletti, D.; Ghini, A.A.; Baggio, R.F.; Garland, M.T.; Burton, G. |
| Filiación: | Departamento de Química Orgánica, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, Buenos Aires, 1428, Argentina Departamento de Física, Comisión Nacional de Energía Atómica, Avda del Libertador 8250, Buenos Aires, 1429, Argentina Departamento de Física, Universidad de Chile, Avda. Blanco Encalada 2008, Casilla 487-3, Santiago, Switzerland |
| Palabras clave: | Chemical bonds; Crystal structure; Fourier transform infrared spectroscopy; Mass spectrometers; Nuclear magnetic resonance spectroscopy; Positive ions; Stereochemistry; X ray crystallography; Regioselective migration; Aromatic hydrocarbons |
| Año: | 2001 |
| Volumen: | 1 |
| Número: | 13 |
| Página de inicio: | 1511 |
| Página de fin: | 1517 |
| DOI: | http://dx.doi.org/10.1039/b102688g |
| Título revista: | Journal of the Chemical Society. Perkin Transactions 1 |
| Título revista abreviado: | J Chem Soc Perkin Trans 1 |
| ISSN: | 14727781 |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14727781_v1_n13_p1511_Nicoletti |
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Citas:
---------- APA ----------
Nicoletti, D., Ghini, A.A., Baggio, R.F., Garland, M.T. & Burton, G. (2001) . Rearrangement of 18-iodo- and 20-iodopregnanes mediated by iodosyl derivatives. Journal of the Chemical Society. Perkin Transactions 1, 1(13), 1511-1517.http://dx.doi.org/10.1039/b102688g
---------- CHICAGO ----------
Nicoletti, D., Ghini, A.A., Baggio, R.F., Garland, M.T., Burton, G. "Rearrangement of 18-iodo- and 20-iodopregnanes mediated by iodosyl derivatives" . Journal of the Chemical Society. Perkin Transactions 1 1, no. 13 (2001) : 1511-1517.http://dx.doi.org/10.1039/b102688g
---------- MLA ----------
Nicoletti, D., Ghini, A.A., Baggio, R.F., Garland, M.T., Burton, G. "Rearrangement of 18-iodo- and 20-iodopregnanes mediated by iodosyl derivatives" . Journal of the Chemical Society. Perkin Transactions 1, vol. 1, no. 13, 2001, pp. 1511-1517.http://dx.doi.org/10.1039/b102688g
---------- VANCOUVER ----------
Nicoletti, D., Ghini, A.A., Baggio, R.F., Garland, M.T., Burton, G. Rearrangement of 18-iodo- and 20-iodopregnanes mediated by iodosyl derivatives. J Chem Soc Perkin Trans 1. 2001;1(13):1511-1517.http://dx.doi.org/10.1039/b102688g
