Artículo
Joselevich, M.; Ghini, A.A.; Burton, G. "6,19-carbon-bridged steroids. Synthesis of 6,19-methano-progesterone" (2003) Organic and Biomolecular Chemistry. 1(6):939-943
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Abstract:
6,19-Methanoprogesterone (4) was synthesized in nine steps from the readily available 3β,20β-diacetyloxy-5α-bromo-6,19,-oxidopregnane (5) in 14% overall yield. The additional carbon atom was introduced by reaction of a C-19 aldehyde with Ph3PCHOCH3 under salt free conditions and subsequent hydrolysis to give the homologous aldehyde. Intramolecular addition of the newly incorporated carbonyl (C-19a) to the olefinic C-6 in ring B was achieved by means of a Prins reaction with TiCl4 as Lewis acid.
Registro:
| Documento: | Artículo |
| Título: | 6,19-carbon-bridged steroids. Synthesis of 6,19-methano-progesterone |
| Autor: | Joselevich, M.; Ghini, A.A.; Burton, G. |
| Filiación: | Depto. de Quimica Orgánica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellon 2, C1428EGA Buenos Aires, Argentina |
| Palabras clave: | Addition reactions; Aldehydes; Atoms; Calculations; Carbon; Conformations; Derivatives; Hydrolysis; Molecular structure; Synthesis (chemical); Diacetyloxybromooxidopregnane; Lewis acid; Methanoprogesterone; Organic compounds; 6,19 methanoprogesterone; 6,19-methanoprogesterone; drug derivative; progesterone; steroid; article; chemical model; chemical structure; synthesis; Models, Chemical; Molecular Structure; Progesterone; Steroids |
| Año: | 2003 |
| Volumen: | 1 |
| Número: | 6 |
| Página de inicio: | 939 |
| Página de fin: | 943 |
| DOI: | http://dx.doi.org/10.1039/b211974a |
| Título revista: | Organic and Biomolecular Chemistry |
| Título revista abreviado: | Org. Biomol. Chem. |
| ISSN: | 14770520 |
| CAS: | progesterone, 57-83-0; 6,19-methanoprogesterone; Progesterone, 57-83-0; Steroids |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14770520_v1_n6_p939_Joselevich |
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Citas:
---------- APA ----------
Joselevich, M., Ghini, A.A. & Burton, G. (2003) . 6,19-carbon-bridged steroids. Synthesis of 6,19-methano-progesterone. Organic and Biomolecular Chemistry, 1(6), 939-943.http://dx.doi.org/10.1039/b211974a
---------- CHICAGO ----------
Joselevich, M., Ghini, A.A., Burton, G. "6,19-carbon-bridged steroids. Synthesis of 6,19-methano-progesterone" . Organic and Biomolecular Chemistry 1, no. 6 (2003) : 939-943.http://dx.doi.org/10.1039/b211974a
---------- MLA ----------
Joselevich, M., Ghini, A.A., Burton, G. "6,19-carbon-bridged steroids. Synthesis of 6,19-methano-progesterone" . Organic and Biomolecular Chemistry, vol. 1, no. 6, 2003, pp. 939-943.http://dx.doi.org/10.1039/b211974a
---------- VANCOUVER ----------
Joselevich, M., Ghini, A.A., Burton, G. 6,19-carbon-bridged steroids. Synthesis of 6,19-methano-progesterone. Org. Biomol. Chem. 2003;1(6):939-943.http://dx.doi.org/10.1039/b211974a
