Abstract:
A general procedure for the synthesis of 1α,11α- and 1β,11α-epoxysteroids is described, using an intramolecular remote functionalization reaction involving the photolysis of 11α-hydroxysteroids in the presence of diacetoxyiodobenzene and iodine. Three 1,11-epoxypregnanes were prepared, two of them (compounds 10 and 14) are conformationally constrained analogues of steroidal hormones, compound 13 is a synthetic precursor of neurosteroids. © 2005 Elsevier Ltd. All rights reserved.
Registro:
Documento: |
Artículo
|
Título: | Synthesis of C(1)-C(11) oxygen-bridged pregnanes |
Autor: | Veleiro, A.S.; Taich, P.J.; Alvarez, L.D.; Di Chenna, P.H.; Burton, G. |
Filiación: | Departamento de Química Orgánica and UMYMFOR (CONICET-FCEN), Facultad de Ciencias Exactas Y Naturales, Ciudad Universitaria, C1428EGA Buenos Aires, Argentina
|
Palabras clave: | 1,11-Epoxypregnane; Diacetoxyiodobenzene; DIB; Remote functionalization reaction; Steroid; hydroxysteroid; iodine; iodobenzene; pregnane derivative; steroid hormone; article; chemical reaction kinetics; drug conformation; drug synthesis; photolysis |
Año: | 2005
|
Volumen: | 46
|
Número: | 24
|
Página de inicio: | 4235
|
Página de fin: | 4238
|
DOI: |
http://dx.doi.org/10.1016/j.tetlet.2005.04.052 |
Título revista: | Tetrahedron Letters
|
Título revista abreviado: | Tetrahedron Lett.
|
ISSN: | 00404039
|
CODEN: | TELEA
|
CAS: | iodine, 7553-56-2; iodobenzene, 591-50-4
|
Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404039_v46_n24_p4235_Veleiro |
Referencias:
- Burton, G., Galigniana, M.D., De Lavallaz, S., Brachet-Cota, A.L., Sproviero, E.M., Ghini, A.A., Lantos, C.P., Damasco, M.C., (1995) Mol. Pharmacol., 47, pp. 535-543
- Galigniana, M.D., Vincent, G.P., Piwien-Pilipuk, G., Burton, G., Lantos, C.P., (2000) Mol. Pharmacol., 58, pp. 58-70
- Vicent, G.P., Monteserín, M.C., Veleiro, A.S., Burton, G., Lantos, C.P., Galigniana, M.D., (1997) Mol. Pharmacol., 52, pp. 749-753
- Veleiro, A.S., Rosenstein, R.E., Jaliffa, C.O., Grilli, M.L., Speroni, F., Burton, G., (2002) Bioorg. Med. Chem. Lett., 13, pp. 343-346
- Kalvoda, J., Heusler, K., (1971) Synthesis, pp. 501-526
- De Armas, P., Concepción, J.I., Francisco, C.G., Hernández, R., Salazar, J.A., Suárez, E., (1989) J. Chem. Soc., Perkin Trans. 1, pp. 405-411
- Kalvoda, J., Anner, G., Arigoni, D., Heusler, K., Miner, H., Jeger, O., Mihailovic, M.L., Wettstein, A., (1961) Helv. Chim. Acta, 44, pp. 186-204
- Nussim, M., Mazur, Y., Sondheimer, F., (1964) J. Org. Chem., 29, pp. 1120-1131
- Bridgeman, J.E., Cherry, P.C., Clegg, A.S., Evans, J.M., Jones, R.H., Kasal, A., Kumar, V., Woodgate, P.D., (1970) J. Chem. Soc. C, pp. 250-257
- note; note; note; note; note
Citas:
---------- APA ----------
Veleiro, A.S., Taich, P.J., Alvarez, L.D., Di Chenna, P.H. & Burton, G.
(2005)
. Synthesis of C(1)-C(11) oxygen-bridged pregnanes. Tetrahedron Letters, 46(24), 4235-4238.
http://dx.doi.org/10.1016/j.tetlet.2005.04.052---------- CHICAGO ----------
Veleiro, A.S., Taich, P.J., Alvarez, L.D., Di Chenna, P.H., Burton, G.
"Synthesis of C(1)-C(11) oxygen-bridged pregnanes"
. Tetrahedron Letters 46, no. 24
(2005) : 4235-4238.
http://dx.doi.org/10.1016/j.tetlet.2005.04.052---------- MLA ----------
Veleiro, A.S., Taich, P.J., Alvarez, L.D., Di Chenna, P.H., Burton, G.
"Synthesis of C(1)-C(11) oxygen-bridged pregnanes"
. Tetrahedron Letters, vol. 46, no. 24, 2005, pp. 4235-4238.
http://dx.doi.org/10.1016/j.tetlet.2005.04.052---------- VANCOUVER ----------
Veleiro, A.S., Taich, P.J., Alvarez, L.D., Di Chenna, P.H., Burton, G. Synthesis of C(1)-C(11) oxygen-bridged pregnanes. Tetrahedron Lett. 2005;46(24):4235-4238.
http://dx.doi.org/10.1016/j.tetlet.2005.04.052