Artículo
Nicoletti, D.; Ghini, A.A.; Burton, G. "Oxidative cyclization of iodo ketones. Synthesis of 6-oxa-5α-pregnane-3,20-dione" (1996) Journal of Organic Chemistry. 61(19):6673-6677
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Abstract:
The steroidal δ- and γ-iodo ketones 1 and 9 were converted to the cyclic hemiketals 3 and 10, by oxidation to the iodoso derivatives with m-CPBA. Spontaneous cyclization of the latter intermediates to the corresponding oxocarbenium ions, followed by stereoselective addition of water, rendered the hemiketals. Depending on the reaction conditions, the five-membered oxocarbenium ion derived from the γ-iodo ketone 9 may add H2O or m-CPBA to give either the hemiketal or a Baeyer-Villiger type product 12, while the oxocarbenium derived from 1 gives exclusively the hemiketal. When the reaction was carried out in dry methanol, methyl ketals were formed. Use of this methodology allowed us to synthesize 6-oxa-5α-pregnanes with and without functionalization at C-19.
Registro:
| Documento: | Artículo |
| Título: | Oxidative cyclization of iodo ketones. Synthesis of 6-oxa-5α-pregnane-3,20-dione |
| Autor: | Nicoletti, D.; Ghini, A.A.; Burton, G. |
| Filiación: | Depto. de Quim. Orgánica, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina |
| Palabras clave: | pregnane derivative; article; drug synthesis; reaction analysis; stereochemistry |
| Año: | 1996 |
| Volumen: | 61 |
| Número: | 19 |
| Página de inicio: | 6673 |
| Página de fin: | 6677 |
| DOI: | http://dx.doi.org/10.1021/jo960108q |
| Título revista: | Journal of Organic Chemistry |
| Título revista abreviado: | J. ORG. CHEM. |
| ISSN: | 00223263 |
| CODEN: | JOCEA |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v61_n19_p6673_Nicoletti |
Referencias:
- Suginome, H., Yamada, S., Wang, J.B., (1990) J. Org. Chem., 55, p. 2170
- Huisman, H.O., (1971) Angew. Chem., Int. Ed. Engl., 10, p. 240
- Nicoletti, D., Ghini, A.A., Brachet-Cota, A.L., Burton, G., (1995) J. Chem. Soc., Perkin Trans. 1, p. 1089
- Lewis, M.D., Cha, J.K., Kishi, Y., (1982) J. Am. Chem. Soc., 104, p. 4976. , and references cited therein
- Deslongchamps, P., (1983) Stereoelectronic Effects in Organic Chemistry, pp. 40-41. , Pergamon Press: Oxford
- Cambie, R.C., Chambers, D., Lindsay, B.G., Rutledge, P.S., Woodgate, P.D., (1980) J. Chem. Soc., Perkin Trans. 1, p. 822
- Macdonald, T.L., Narasimhan, N., Burka, L.T., (1980) J. Am. Chem. Soc., 102, p. 7760. , and references cited therein
- Lee, J., Oh, J., Jin, S.-J., Choi, J.-R., Atwood, J.L., Cha, J.K., (1994) J. Org. Chem., 59, p. 6955. , and references cited therein
- Kotsuki, H., Ushio, Y., Yoshimura, N., Ochi, M., (1987) J. Org. Chem., 52, p. 2594
- Kraus, G.A., Frazier, K.A., Roth, B.D., Taschner, M.J., Neuenschwander, K., (1981) J. Org. Chem., 46, p. 2417. , and Lewis et al. in ref 4
- note; Barton, D.H.R., Blundell, P., Dorchak, J., Jang, D.O., Jaszberenyi, J.C., (1991) Tetrahedron, 47, p. 8969. , and references cited therein
- Cheng, Y.-S., Liu, W.-L., Chen, S.-H., (1980) Synthesis, p. 223
- Woodward, R.B., Brutcher, F.V., (1958) J. Am. Chem. Soc., 80, p. 209
- Choay, P., Monneret, C., Khuong-Hun, Q., (1973) Bull. Soc. Chim. Fr., p. 1456
- Kirk, D.N., Rajagopalan, M.S., (1975) J. Chem. Soc., Perkin Trans. 1, p. 1860
- Barton, D.H.R., Day, M.J., Hesse, R.H., Pechet, M.M., (1975) J. Chem. Soc., Perkin Trans. 1, p. 2252
- Das, R., Kirk, D.N., (1984) J. Chem. Soc., Perkin Trans. 1, p. 1821
- March, J., (1992) Advanced Organic Chemistry, 4th Ed., pp. 1098-1099. , John Wiley & Sons: New York
- note; note; Benedetti, M.O.V., Burton, G., (1992) Org. Prep. Proced. Int., 24, p. 701. , and references cited therein
- Pappo, R., (1962) Chem. Abstr., 56, pp. 12988h. , U.S. Patent 3 017 410, 1962
- Pappo, R., (1960) Chem. Abstr., 54, pp. 243Id. , U.S. Patent 2 907 758, 1959
Citas:
---------- APA ----------
Nicoletti, D., Ghini, A.A. & Burton, G. (1996) . Oxidative cyclization of iodo ketones. Synthesis of 6-oxa-5α-pregnane-3,20-dione. Journal of Organic Chemistry, 61(19), 6673-6677.http://dx.doi.org/10.1021/jo960108q
---------- CHICAGO ----------
Nicoletti, D., Ghini, A.A., Burton, G. "Oxidative cyclization of iodo ketones. Synthesis of 6-oxa-5α-pregnane-3,20-dione" . Journal of Organic Chemistry 61, no. 19 (1996) : 6673-6677.http://dx.doi.org/10.1021/jo960108q
---------- MLA ----------
Nicoletti, D., Ghini, A.A., Burton, G. "Oxidative cyclization of iodo ketones. Synthesis of 6-oxa-5α-pregnane-3,20-dione" . Journal of Organic Chemistry, vol. 61, no. 19, 1996, pp. 6673-6677.http://dx.doi.org/10.1021/jo960108q
---------- VANCOUVER ----------
Nicoletti, D., Ghini, A.A., Burton, G. Oxidative cyclization of iodo ketones. Synthesis of 6-oxa-5α-pregnane-3,20-dione. J. ORG. CHEM. 1996;61(19):6673-6677.http://dx.doi.org/10.1021/jo960108q
