Artículo
Di Chenna, P.H.; Dauban, P.; Ghini, A.; Baggio, R.; Garland, M.T.; Burton, G.; Dodd, R.H. "PhI=NSes mediated aziridination of 11-pregnane derivatives: Synthesis of an 11,12-aziridino analogue of neuroactive steroids" (2003) Tetrahedron. 59(7):1009-1014
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Abstract:
Reaction of 11-pregnene-3,20-dione (6) or 3-α-acetoxy-11-pregnen-20-one (12) with trimethylsilylethanesulfonyl ('Ses') iminoiodinane 5 in the presence of copper (I) triflate gave the corresponding α,α-11,12-aziridino steroids 7 and 13 in 53 and 45% yields, respectively. The Ses group of each compound was removed using the TASF reagent and the resulting free aziridine NH was methylated to afford the 11α,12α-N-methyl aziridinosteroids 9 and 15, respectively. The latter is a conformationally constrained analogue of the endogenous neurosteroid pregnanolone (1). © 2003 Elsevier Science Ltd. All rights reserved.
Registro:
| Documento: | Artículo |
| Título: | PhI=NSes mediated aziridination of 11-pregnane derivatives: Synthesis of an 11,12-aziridino analogue of neuroactive steroids |
| Autor: | Di Chenna, P.H.; Dauban, P.; Ghini, A.; Baggio, R.; Garland, M.T.; Burton, G.; Dodd, R.H. |
| Filiación: | Depto. de Quím. Orgán., Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, Argentina Inst. de Chim. des Substances N., CNRS, 91198 Gif-sur-Yvette Cedex, France Departamento de Física, Comn. Nac. de Energia Atómica, Av. del Libertador 8250, C1429 Buenos Aires, Argentina Departamento de Física, Fac. de Cie. Fis. y Matemat., Universidad de Chile, Av. Blanco Encalada 2008, Casilla 487-3 Santiago, Chile |
| Palabras clave: | Aziridine; Iminoiodinane; Ses group; Steroid; 3alpha acetoxy 5beta h 11 pregnen 20 one; 3alpha acetoxy n [2 (trimethylsilyl)ethanesulfonyl] 11alpha,12alpha aziridino 5beta h pregnan 20 one; 3alpha hydroxy n methyl 11alpha,12alpha aziridino 5beta h pregnan 20 one; alkane derivative; aziridine derivative; copper derivative; eltanolone; iodine derivative; ketone derivative; n [2 (trimethylsilyl)ethanesulfonyl] 11alpha,12alpha aziridino 5beta h pregnane 3,20 dione; n methyl 11alpha,12alpha aziridino 5beta h pregnane 3,20 dione; neurosteroid; pregnane derivative; trimethylsilyl derivative; unclassified drug; article; aziridination; catalysis; chemical reaction; drug conformation; drug synthesis; methylation; priority journal; proton nuclear magnetic resonance; stereochemistry; X ray crystallography |
| Año: | 2003 |
| Volumen: | 59 |
| Número: | 7 |
| Página de inicio: | 1009 |
| Página de fin: | 1014 |
| DOI: | http://dx.doi.org/10.1016/S0040-4020(02)01655-1 |
| Título revista: | Tetrahedron |
| Título revista abreviado: | Tetrahedron |
| ISSN: | 00404020 |
| CODEN: | TETRA |
| CAS: | eltanolone, 128-20-1 |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v59_n7_p1009_DiChenna |
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Citas:
---------- APA ----------
Di Chenna, P.H., Dauban, P., Ghini, A., Baggio, R., Garland, M.T., Burton, G. & Dodd, R.H. (2003) . PhI=NSes mediated aziridination of 11-pregnane derivatives: Synthesis of an 11,12-aziridino analogue of neuroactive steroids. Tetrahedron, 59(7), 1009-1014.http://dx.doi.org/10.1016/S0040-4020(02)01655-1
---------- CHICAGO ----------
Di Chenna, P.H., Dauban, P., Ghini, A., Baggio, R., Garland, M.T., Burton, G., et al. "PhI=NSes mediated aziridination of 11-pregnane derivatives: Synthesis of an 11,12-aziridino analogue of neuroactive steroids" . Tetrahedron 59, no. 7 (2003) : 1009-1014.http://dx.doi.org/10.1016/S0040-4020(02)01655-1
---------- MLA ----------
Di Chenna, P.H., Dauban, P., Ghini, A., Baggio, R., Garland, M.T., Burton, G., et al. "PhI=NSes mediated aziridination of 11-pregnane derivatives: Synthesis of an 11,12-aziridino analogue of neuroactive steroids" . Tetrahedron, vol. 59, no. 7, 2003, pp. 1009-1014.http://dx.doi.org/10.1016/S0040-4020(02)01655-1
---------- VANCOUVER ----------
Di Chenna, P.H., Dauban, P., Ghini, A., Baggio, R., Garland, M.T., Burton, G., et al. PhI=NSes mediated aziridination of 11-pregnane derivatives: Synthesis of an 11,12-aziridino analogue of neuroactive steroids. Tetrahedron. 2003;59(7):1009-1014.http://dx.doi.org/10.1016/S0040-4020(02)01655-1
