Artículo
Teme Centurión, O.M.; Galagovsky, L.R. "Alternative synthesis of (24S)-homoethylcastasterone from stigmasterol" (1998) Anales des la Asociacion Quimica Argentina. 86(3-6):104-109
Estamos trabajando para incorporar este artículo al repositorio
Consulte la política de Acceso Abierto del editor
Abstract:
24(S)-Homoethylcastasterone belongs to the group of natural products named brassinosteroids. This work reports its synthesis from stigmasterol through a new pathway which involves a reductive opening of a 5β,6β-steroidal epoxide derivative. Key intermediate compound 4a also allows to develop pathways for the synthesis of highly active C-3 natural oxygenated brassinosteroids.
Registro:
| Documento: | Artículo |
| Título: | Alternative synthesis of (24S)-homoethylcastasterone from stigmasterol |
| Autor: | Teme Centurión, O.M.; Galagovsky, L.R. |
| Filiación: | Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, 1428 Buenos Aires, Argentina |
| Año: | 1998 |
| Volumen: | 86 |
| Número: | 3-6 |
| Página de inicio: | 104 |
| Página de fin: | 109 |
| Título revista: | Anales des la Asociacion Quimica Argentina |
| ISSN: | 03650375 |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03650375_v86_n3-6_p104_TemeCenturion |
Referencias:
- Grove, M.D., Spencer, G.F., Rohwedder, W.K., Mandava, N., Worley, J.F., Warthen Jr., J.D., Steffens, G.L., Cook Jr., J.C., (1979) Nature, 281, p. 216
- Mandava, N.B., (1988) Annu. Rev. Plant. Physiol. Plant Mol. Biol., 39, p. 23
- Kim, S.-K., Natural Occurrences of Brassinosteroids in Brassinosteroids (1991) ACS Symp. Ser., p. 474. , H. G. Cutler, T. Yokota and G. Adam, Eds. ch. 3
- Kamuro, Y., Takatsuto, S., Capability for and Problems of Practical Uses of Brassinosteroids in Brassinosteroids (1991) ACS Symp. Ser., p. 474. , H. C. Cutler, T. Yokota and G. Adam, Eds, ch. 25
- Clouse, S.D., Hall, A.F., Langford, M., McMorris, T.C., Baker, M.E., (1993) J. Plant Growth Regul., 12, p. 61
- Li, J., Nagpal, P., Vitart, V., McMorris, T.C., Chory, J., (1996) Science, 272, p. 398
- McMorris, T.C., Patil, P.A., Chavez, R.G., Baker, M.E., Clouse, S.D., (1994) Phytochemistry, 36, p. 585
- Ishiguro, M., Takatsuto, S., Morisaki, M., Ikekawa, N., (1980) J. Chem. Soc. Chem. Comm., p. 962
- Takatsuto, S., Ying, B., Morisaki, M., Ikekawa, N., (1981) Chem. Pharm. Bull., 29, p. 903
- Takatsuto, S., Yasawa, N., Ishiguro, M., Morisaki, M., Ikekawa, N., (1984) J. Chem Soc. Perkin Trans. 1, p. 139
- Teme Centurión, O.M., (1997), Doctoral Dissertation, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, To be published elsewhere; Takatsuto, S., Ikekawa, N., (1983) J. Chem. Soc. Perkin Trans. 1, p. 2133
- Sakakibara, M., Mori, K., (1984) Agric. Biol. Chem., 48, p. 745
- Anastasia, M., Allevi, P., Ciuffreda, P., Fiechi, A., Sacla, A., (1984) J. Org. Chem., 49, p. 4297
- Kametani, T., Keino, K., Kigawa, M., Tsubuki, M., Honda, T., (1989) Tetrahedron Lett., 30, p. 3141
- Yokota, T., Watanabe, S., Ogino, Y., Yamaguchi, I., Takahashi, N., (1990) J. Plant. Growth Regul., 9, p. 151
- Mc Morris, T.C., Chavez, R.C., Patil, P.A., (1996) J. Chem. Soc. Perkin Trans. 1, p. 295
- Syamala, M.S., Das, J., Baskaran, S., Chandrasekaran, S., (1992) J. Org. Chem., 57, p. 1928
- House, H.O., (1972) Modern Synthetic Reactions, , Benjamin, Inc., Menlo Park, California
- Sankawa, U., Sato, T., (1978) Tetrahedron Lett., 11, p. 981
- Mark, M., Rerick, N., Eliel, E.L., (1962) J. Am. Chem. Soc., 84, p. 2356
- Brown, H.C., Yoon, N.M., (1968) J. Am. Chem. Soc., 90, p. 2688
- Zhou, W., (1989) Pure & Applied Chem., 61, p. 31
- Galagovsky, L.R., Burton, G., Gros, E.G., (1989) Z. Naturforsch., 44 B, p. 806
- Teme Centurión, O.M., (1997), Tesis Doctoral, Departamento de Química Orgánica, Facultad de Ciencias Exactas y naturales, Universidad de Buenos Aires; Crispino, G.A., Makita, A., Wang, Z.-M., Sharpless, K.B., (1994) Tetrahedron Lett., 35, p. 543
- Gladu, P.K., Patterson, G.W., Wikfors, G.H., Lusby, W.R., (1991) Lipids, 26, p. 656
- Fernández, M.I., Pedro, J.R., Seoane, E., (1983) Phytochemistry, 22, p. 2087
- Wada, K., Marumo, S., (1981) Agric. Biol. Chem., 45, p. 2579
- Takatsuto, S., Ikekawa, N., (1982) Chem. Pharm. Bull., 30, p. 4181
- Mitra, R.B., Kapoor, V.M., (1985) Synth. Commun., 15, p. 1087
Citas:
---------- APA ----------
Teme Centurión, O.M. & Galagovsky, L.R. (1998) . Alternative synthesis of (24S)-homoethylcastasterone from stigmasterol. Anales des la Asociacion Quimica Argentina, 86(3-6), 104-109.Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03650375_v86_n3-6_p104_TemeCenturion [ ]
---------- CHICAGO ----------
Teme Centurión, O.M., Galagovsky, L.R. "Alternative synthesis of (24S)-homoethylcastasterone from stigmasterol" . Anales des la Asociacion Quimica Argentina 86, no. 3-6 (1998) : 104-109.Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03650375_v86_n3-6_p104_TemeCenturion [ ]
---------- MLA ----------
Teme Centurión, O.M., Galagovsky, L.R. "Alternative synthesis of (24S)-homoethylcastasterone from stigmasterol" . Anales des la Asociacion Quimica Argentina, vol. 86, no. 3-6, 1998, pp. 104-109.Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03650375_v86_n3-6_p104_TemeCenturion [ ]
---------- VANCOUVER ----------
Teme Centurión, O.M., Galagovsky, L.R. Alternative synthesis of (24S)-homoethylcastasterone from stigmasterol. 1998;86(3-6):104-109.Available from: https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03650375_v86_n3-6_p104_TemeCenturion [ ]
