Oxidative cyclization of iodo ketones. Synthesis of 6-oxa-5α-pregnane-3,20-dione
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 he...
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1996
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| LEADER | 04953caa a22006377a 4500 | ||
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| 001 | PAPER-18799 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518205010.0 | ||
| 008 | 190411s1996 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-0029819311 | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a JOCEA | ||
| 100 | 1 | |a Nicoletti, D. | |
| 245 | 1 | 0 | |a Oxidative cyclization of iodo ketones. Synthesis of 6-oxa-5α-pregnane-3,20-dione |
| 260 | |c 1996 | ||
| 270 | 1 | 0 | |m Burton, G.; Departamento de Quimica Organica, Fac de Cie. Exactas y Naturales, Universidad de Buenos Aires, Pabellon 2, 1428 Buenos Aires, Argentina |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a Suginome, H., Yamada, S., Wang, J.B., (1990) J. Org. Chem., 55, p. 2170 | ||
| 504 | |a Huisman, H.O., (1971) Angew. Chem., Int. Ed. Engl., 10, p. 240 | ||
| 504 | |a Nicoletti, D., Ghini, A.A., Brachet-Cota, A.L., Burton, G., (1995) J. Chem. Soc., Perkin Trans. 1, p. 1089 | ||
| 504 | |a Lewis, M.D., Cha, J.K., Kishi, Y., (1982) J. Am. Chem. Soc., 104, p. 4976. , and references cited therein | ||
| 504 | |a Deslongchamps, P., (1983) Stereoelectronic Effects in Organic Chemistry, pp. 40-41. , Pergamon Press: Oxford | ||
| 504 | |a Cambie, R.C., Chambers, D., Lindsay, B.G., Rutledge, P.S., Woodgate, P.D., (1980) J. Chem. Soc., Perkin Trans. 1, p. 822 | ||
| 504 | |a Macdonald, T.L., Narasimhan, N., Burka, L.T., (1980) J. Am. Chem. Soc., 102, p. 7760. , and references cited therein | ||
| 504 | |a 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 | ||
| 504 | |a Kotsuki, H., Ushio, Y., Yoshimura, N., Ochi, M., (1987) J. Org. Chem., 52, p. 2594 | ||
| 504 | |a 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 | ||
| 504 | |a note; Barton, D.H.R., Blundell, P., Dorchak, J., Jang, D.O., Jaszberenyi, J.C., (1991) Tetrahedron, 47, p. 8969. , and references cited therein | ||
| 504 | |a Cheng, Y.-S., Liu, W.-L., Chen, S.-H., (1980) Synthesis, p. 223 | ||
| 504 | |a Woodward, R.B., Brutcher, F.V., (1958) J. Am. Chem. Soc., 80, p. 209 | ||
| 504 | |a Choay, P., Monneret, C., Khuong-Hun, Q., (1973) Bull. Soc. Chim. Fr., p. 1456 | ||
| 504 | |a Kirk, D.N., Rajagopalan, M.S., (1975) J. Chem. Soc., Perkin Trans. 1, p. 1860 | ||
| 504 | |a Barton, D.H.R., Day, M.J., Hesse, R.H., Pechet, M.M., (1975) J. Chem. Soc., Perkin Trans. 1, p. 2252 | ||
| 504 | |a Das, R., Kirk, D.N., (1984) J. Chem. Soc., Perkin Trans. 1, p. 1821 | ||
| 504 | |a March, J., (1992) Advanced Organic Chemistry, 4th Ed., pp. 1098-1099. , John Wiley & Sons: New York | ||
| 504 | |a note; note; Benedetti, M.O.V., Burton, G., (1992) Org. Prep. Proced. Int., 24, p. 701. , and references cited therein | ||
| 504 | |a Pappo, R., (1962) Chem. Abstr., 56, pp. 12988h. , U.S. Patent 3 017 410, 1962 | ||
| 504 | |a Pappo, R., (1960) Chem. Abstr., 54, pp. 243Id. , U.S. Patent 2 907 758, 1959 | ||
| 520 | 3 | |a 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. |l eng | |
| 593 | |a Depto. de Quim. Orgánica, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina | ||
| 690 | 1 | 0 | |a PREGNANE DERIVATIVE |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a DRUG SYNTHESIS |
| 690 | 1 | 0 | |a REACTION ANALYSIS |
| 690 | 1 | 0 | |a STEREOCHEMISTRY |
| 700 | 1 | |a Ghini, A.A. | |
| 700 | 1 | |a Burton, G. | |
| 773 | 0 | |d 1996 |g v. 61 |h pp. 6673-6677 |k n. 19 |p J. ORG. CHEM. |x 00223263 |w (AR-BaUEN)CENRE-337 |t Journal of Organic Chemistry | |
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| 856 | 4 | 0 | |u https://doi.org/10.1021/jo960108q |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_00223263_v61_n19_p6673_Nicoletti |y Handle |
| 856 | 4 | 0 | |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v61_n19_p6673_Nicoletti |y Registro en la Biblioteca Digital |
| 961 | |a paper_00223263_v61_n19_p6673_Nicoletti |b paper |c PE | ||
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| 963 | |a VARI | ||
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