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Abstract:

1,11-Epoxysteroids may be obtained by an intramolecular remote functionalization using Suarez reagent (diacetoxyiodobenzene/I 2) and irradiation with visible light. We have found that photolysis with visible light may be advantageously replaced by microwave irradiation to prepare 1,11-oxygen bridges resulting in higher yields and shorter reaction times especially in the case of sensitive substrates. Both methodologies were compared on a set of representative 11-α-hydroxypregnanes (3, 8, 10 and 11). © 2011 Elsevier Inc. All rights reserved.

Registro:

Documento: Artículo
Título:Microwave assisted preparation of C(1)-C(11) oxygen-bridged pregnanes
Autor:Alvarez, L.D.; Sonego, J.M.; Veleiro, A.S.; Burton, G.
Filiación:Departamento de Química Orgánica and UMYMFOR (CONICET-UBA), Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, Pabellón 2, C1428EGA Ciudad de Buenos Aires, Argentina
Palabras clave:1,11-Epoxypregnane; Diacetoxyiodobenzene; Microwave irradiation; Remote functionalization; 11alpha hydroxyprogesterone; 3beta,20 diacetoxy 1alpha iodo 5alpha pregnan 11alpha ol; 3beta,20 diacetoxy 1alpha,11alpha epoxy 4 pregnene; 3beta,20 diacetoxy 4 pregnen 11alpha ol; 3beta,20 diacetoxy 5a pregnan 11alpha ol; oxygen; pregnane derivative; unclassified drug; article; light; methodology; microwave irradiation; photolysis; reaction time; Microwaves; Models, Molecular; Molecular Conformation; Oxygen; Pregnanes
Año:2011
Volumen:76
Número:13
Página de inicio:1458
Página de fin:1464
DOI: http://dx.doi.org/10.1016/j.steroids.2011.07.016
Título revista:Steroids
Título revista abreviado:Steroids
ISSN:0039128X
CODEN:STEDA
CAS:11alpha hydroxyprogesterone, 80-75-1; oxygen, 7782-44-7; Oxygen, 7782-44-7; Pregnanes
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v76_n13_p1458_Alvarez

Referencias:

  • Veleiro, A.S., Pecci, A., Monteserin, M.C., Baggio, R., Garland, M.T., Lantos, C.P., Burton, G., 6,19-Sulfur-bridged progesterone analogues with antiimmunosuppressive activity (2005) Journal of Medicinal Chemistry, 48 (18), pp. 5675-5683. , DOI 10.1021/jm049266x
  • Alvarez, L.D., Marti, M.A., Veleiro, A.S., Presman, D.M., Estrin, D.A., Pecci, A., Burton, G., Exploring the molecular basis of action of the passive antiglucocorticoid 21-hydroxy-6,19-epoxyprogesterone (2008) Journal of Medicinal Chemistry, 51 (5), pp. 1352-1360. , DOI 10.1021/jm800007w
  • Pecci, A., Alvarez, L.D., Veleiro, A.S., Ceballos, N.R., Lantos, C.P., Burton, G., New lead compounds in the search for pure antiglucocorticoids and the dissociation of antiglucocorticoid effects (2009) J Steroid Biochem Mol Biol, 113, pp. 155-162
  • Komatsu, S., Yaguchi, A., Yamashita, K., Nagaoka, M., Numazawa, M., 6β,19-Bridged androstenedione analogs as aromatase inhibitors (2009) Steroids, 74, pp. 884-889
  • Veleiro, A.S., Taich, P.J., Alvarez, L.D., Di Chenna, P.H., Burton, G., Synthesis of C(1)-C(11) oxygen-bridged pregnanes (2005) Tetrahedron Letters, 46 (24), pp. 4235-4238. , DOI 10.1016/j.tetlet.2005.04.052, PII S0040403905008592
  • Alvarez, L.D., Veleiro, A.S., Baggio, R.F., Garland, M.T., Edelsztein, V.C., Coirini, H., Burton, G., Synthesis and GABA A receptor activity of oxygen-bridged neurosteroid analogs (2008) Bioorganic and Medicinal Chemistry, 16 (7), pp. 3831-3838. , DOI 10.1016/j.bmc.2008.01.048, PII S0968089608000680
  • Costa, S.C.P., Moreno, M.J.S.M., SaeMelo, M.L., Campos Neves, A.S., Ultrasound assisted remote functionalization of non-activated carbon atoms: Efficient in situ formation of tetrahydrofurans by sonolysis of bromohydrins with (diacetoxyiodo)benzene/I 2 (1999) Tetrahedron Letters, 40 (49), pp. 8711-8714. , DOI 10.1016/S0040-4039(99)01849-3, PII S0040403999018493
  • Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., (2003) Gaussian 03. Revision B.05, , Gaussian Inc. Pittsburgh, PA
  • Kalvoda, J., Heusler, K., Die Hypojodit-Reaktion (Verfahren zur intramolekularen Substitution an nicht-aktivierten C-Atomen) (1971) Synthesis, pp. 501-526
  • Benedetti, M.O.V., Monteagudo, E.S., Burton, G., Improved procedure for the cleavage of alkyl and benzyl ethers with zinc iodide (1990) J Chem Res (S), pp. 248-249

Citas:

---------- APA ----------
Alvarez, L.D., Sonego, J.M., Veleiro, A.S. & Burton, G. (2011) . Microwave assisted preparation of C(1)-C(11) oxygen-bridged pregnanes. Steroids, 76(13), 1458-1464.
http://dx.doi.org/10.1016/j.steroids.2011.07.016
---------- CHICAGO ----------
Alvarez, L.D., Sonego, J.M., Veleiro, A.S., Burton, G. "Microwave assisted preparation of C(1)-C(11) oxygen-bridged pregnanes" . Steroids 76, no. 13 (2011) : 1458-1464.
http://dx.doi.org/10.1016/j.steroids.2011.07.016
---------- MLA ----------
Alvarez, L.D., Sonego, J.M., Veleiro, A.S., Burton, G. "Microwave assisted preparation of C(1)-C(11) oxygen-bridged pregnanes" . Steroids, vol. 76, no. 13, 2011, pp. 1458-1464.
http://dx.doi.org/10.1016/j.steroids.2011.07.016
---------- VANCOUVER ----------
Alvarez, L.D., Sonego, J.M., Veleiro, A.S., Burton, G. Microwave assisted preparation of C(1)-C(11) oxygen-bridged pregnanes. Steroids. 2011;76(13):1458-1464.
http://dx.doi.org/10.1016/j.steroids.2011.07.016