Stereospecific synthesis of steroidal 20,16-γ-carbolactones
Two strategies have been explored for the synthesis of steroidal 20,16- γ-carbolactones from the corresponding 17-ketoandrostane. A highly efficient, stereospecific protocol has been developed for the β-oriented cis-γ-lactone, based on a Michael addition of cyanide to a conjugated ketone. A differen...
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| Formato: | Capítulo de libro |
| Lenguaje: | Inglés |
| Publicado: |
Marcel Dekker Inc.
1998
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| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
| Aporte de: | Registro referencial: Solicitar el recurso aquí |
| LEADER | 04603caa a22006977a 4500 | ||
|---|---|---|---|
| 001 | PAPER-3015 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518203229.0 | ||
| 008 | 190411s1998 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-0031658233 | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a SYNCA | ||
| 100 | 1 | |a Bruttomesso, A.C. | |
| 245 | 1 | 0 | |a Stereospecific synthesis of steroidal 20,16-γ-carbolactones |
| 260 | |b Marcel Dekker Inc. |c 1998 | ||
| 270 | 1 | 0 | |m Gros, E.G.; Departamento de Quimica Organica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a Rahman, A., Choudhary, M.I., (1997) Nat. Prod. Rep., 14, p. 191 | ||
| 504 | |a Fieser, L.F., Fieser, M., (1959) Steroids, pp. 810-846. , Reinhold Publishing Corp., New York, NY | ||
| 504 | |a Basu, N., Rastogi, R.P., (1967) Phytochemistry, 6, p. 1249 | ||
| 504 | |a Shakirov, R., Yunusov, M.S., (1990) Nat. Prod. Rep., 7, p. 557 | ||
| 504 | |a Kessar, S.V., Rampal, A.L., Gupta, Y.P., (1968) Tetrahedron, 24, p. 905. , and references cited therein | ||
| 504 | |a Homan, R., Krause, B.R., (1997) Current Pharmacological Design, 3, p. 29 | ||
| 504 | |a Mazur, Y., Danieli, N., Sondheimer, F., (1960) J. Am. Chem. Soc., 82, p. 5889 | ||
| 504 | |a note; Oka, K., Hara, S., (1978) J. Org. Chem., 43, p. 4408 | ||
| 504 | |a Barton, D.H.R., Beckwith, A.L.J., Goosen, A., (1965) J. Chem. Soc., p. 181 | ||
| 504 | |a González, A.G., Francisco, C.G., Barreira, R.F., Lopez, E.S., (1971) An. Quím., 67, p. 433 | ||
| 504 | |a (1971) Chem. Abst., 75, pp. 115890n | ||
| 504 | |a Chakravarty, A.K., Das, B., Pakrashi, S.C., (1982) Phytochemistry, 21, p. 2083 | ||
| 504 | |a Nagaoka, T., Yoshihara, T., Sakamura, S., (1987) Phytochemistry, 26, p. 2113 | ||
| 504 | |a Gonzalez, A.G., Freire, R., Francisco, C.G., Salazar, J.A., Suárez, E., (1973) Tetrahedron, 29, p. 1731 | ||
| 504 | |a Doller, D., Gros, E.G., (1990) Synth. Commun., 20, p. 3115 | ||
| 504 | |a Schnuff, N.R., Trost, B.M., (1983) J. Org. Chem., 48, p. 1404 | ||
| 504 | |a Kobayashi, N., Hisada, A., Shimada, K., (1993) J. Chem. Soc. Perkin Trans. I, p. 31 | ||
| 504 | |a Clark, I.M., Denney, W.A., Jones, B.R.H., Meakins, G.D., Pendlebury, A., Pinhey, J.T., (1972) J. Chem. Soc. Perkin Trans. I, p. 2765 | ||
| 504 | |a Brown, H.C., McFarlin, R.F., (1958) J. Am. Chem. Soc., 80, p. 5372 | ||
| 504 | |a Aristoff, P.A., Johnson, P.D., Harrison, A.W., (1985) J. Am. Chem. Soc., 107, p. 7967 | ||
| 504 | |a Sato, Y., Ikekawa, N., (1961) J. Org. Chem., 26, p. 5058 | ||
| 504 | |a note; Ito, Y., Kato, H., Imai, H., Saegasa, T., (1982) J. Am. Chem. Soc., 104, p. 6449 | ||
| 520 | 3 | |a Two strategies have been explored for the synthesis of steroidal 20,16- γ-carbolactones from the corresponding 17-ketoandrostane. A highly efficient, stereospecific protocol has been developed for the β-oriented cis-γ-lactone, based on a Michael addition of cyanide to a conjugated ketone. A different approach, involving prior attachment of a 3-carbon side chain on C-17 of a 17-oxo-16β-acetoxy-androstane led to the epimeric, α- oriented lactone. |l eng | |
| 593 | |a Depto. de Quím. Orgán., Fac. de Ciencias Exactas y Naturales, Ciudad Universitaria, 1428 Buenos Aires, Argentina | ||
| 593 | |a Schering-Plough Research Institute, 2015 Galloping Hill Road, Kenilworth, NJ 07033, United States | ||
| 690 | 1 | 0 | |a 20,16 GAMMA CARBOLACTONE DERIVATIVE |
| 690 | 1 | 0 | |a ANDROSTANE DERIVATIVE |
| 690 | 1 | 0 | |a LACTONE DERIVATIVE |
| 690 | 1 | 0 | |a UNCLASSIFIED DRUG |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a DRUG STRUCTURE |
| 690 | 1 | 0 | |a DRUG SYNTHESIS |
| 690 | 1 | 0 | |a NUCLEAR OVERHAUSER EFFECT |
| 690 | 1 | 0 | |a STEREOSPECIFICITY |
| 700 | 1 | |a Doller, D. | |
| 700 | 1 | |a Gros, E.G. | |
| 773 | 0 | |d Marcel Dekker Inc., 1998 |g v. 28 |h pp. 4043-4057 |k n. 21 |p Synth. Commun. |x 00397911 |t Synthetic Communications | |
| 856 | 4 | 1 | |u https://www.scopus.com/inward/record.uri?eid=2-s2.0-0031658233&doi=10.1080%2f00397919808004965&partnerID=40&md5=4d3c7aee412234b1cd4cfbd0f4de7e70 |y Registro en Scopus |
| 856 | 4 | 0 | |u https://doi.org/10.1080/00397919808004965 |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_00397911_v28_n21_p4043_Bruttomesso |y Handle |
| 856 | 4 | 0 | |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00397911_v28_n21_p4043_Bruttomesso |y Registro en la Biblioteca Digital |
| 961 | |a paper_00397911_v28_n21_p4043_Bruttomesso |b paper |c PE | ||
| 962 | |a info:eu-repo/semantics/article |a info:ar-repo/semantics/artículo |b info:eu-repo/semantics/publishedVersion | ||
| 999 | |c 63968 | ||