Syntheses of 21-hydroxy-11,19-oxidopregn-4-ene-3,20-dione and 21-hydroxy-6,19-oxidopregn-4-ene-3,20-dione
The 21-hydroxy analogues of 11,19-oxidoprogesterone and 6,19-oxidoprogesterone have been synthesized from readily available materials. Hydroxylation at C-21 was effected with iodosobenzene (from phenyliodosodiacetate and methanolic potassium hydroxide) on a 20-ketopregnane. For the 11,19-oxido deriv...
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todo:paper_0039128X_v60_n3_p268_Veleiro2023-10-03T14:49:22Z Syntheses of 21-hydroxy-11,19-oxidopregn-4-ene-3,20-dione and 21-hydroxy-6,19-oxidopregn-4-ene-3,20-dione Veleiro, A.S. Nevado, M.V. Monteserín, M.C. Burton, G. 21-hydroxylation oxido-bridged pregnanes 21 hydroxy 11,19 oxidopregn 4 ene 3,20 dione 21 hydroxy 6,19 oxidopregn 4 ene 3,20 dione 21-hydroxy-11,19-oxidopregn-4-ene-3,20-dione 21-hydroxy-6,19-oxidopregn-4-ene-3,20-dione aldosterone drug derivative progesterone 21 hydroxy 11,19 oxidopregn 4 ene 3,20 dione 21 hydroxy 6,19 oxidopregn 4 ene 3,20 dione deoxycorticosterone mineralocorticoid receptor unclassified drug acetylation article chemical structure chemistry hydroxylation oxidation reduction reaction synthesis drug structure drug synthesis steroidogenesis Acetylation Aldosterone Hydroxylation Molecular Structure Oxidation-Reduction Progesterone Support, Non-U.S. Gov't The 21-hydroxy analogues of 11,19-oxidoprogesterone and 6,19-oxidoprogesterone have been synthesized from readily available materials. Hydroxylation at C-21 was effected with iodosobenzene (from phenyliodosodiacetate and methanolic potassium hydroxide) on a 20-ketopregnane. For the 11,19-oxido derivative, the hydroxylation was carried out on a precursor containing the oxido-bridge. This approach was not adequate for the 6,19-oxido steroid due to the very low yields encountered; hence in the latter case the order of introduction of the C-21 functionality and the oxido-bridge was reversed. © 1995. Fil:Veleiro, A.S. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Burton, G. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_0039128X_v60_n3_p268_Veleiro |
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Universidad de Buenos Aires |
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I-28 |
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R-134 |
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
21-hydroxylation oxido-bridged pregnanes 21 hydroxy 11,19 oxidopregn 4 ene 3,20 dione 21 hydroxy 6,19 oxidopregn 4 ene 3,20 dione 21-hydroxy-11,19-oxidopregn-4-ene-3,20-dione 21-hydroxy-6,19-oxidopregn-4-ene-3,20-dione aldosterone drug derivative progesterone 21 hydroxy 11,19 oxidopregn 4 ene 3,20 dione 21 hydroxy 6,19 oxidopregn 4 ene 3,20 dione deoxycorticosterone mineralocorticoid receptor unclassified drug acetylation article chemical structure chemistry hydroxylation oxidation reduction reaction synthesis drug structure drug synthesis steroidogenesis Acetylation Aldosterone Hydroxylation Molecular Structure Oxidation-Reduction Progesterone Support, Non-U.S. Gov't |
| spellingShingle |
21-hydroxylation oxido-bridged pregnanes 21 hydroxy 11,19 oxidopregn 4 ene 3,20 dione 21 hydroxy 6,19 oxidopregn 4 ene 3,20 dione 21-hydroxy-11,19-oxidopregn-4-ene-3,20-dione 21-hydroxy-6,19-oxidopregn-4-ene-3,20-dione aldosterone drug derivative progesterone 21 hydroxy 11,19 oxidopregn 4 ene 3,20 dione 21 hydroxy 6,19 oxidopregn 4 ene 3,20 dione deoxycorticosterone mineralocorticoid receptor unclassified drug acetylation article chemical structure chemistry hydroxylation oxidation reduction reaction synthesis drug structure drug synthesis steroidogenesis Acetylation Aldosterone Hydroxylation Molecular Structure Oxidation-Reduction Progesterone Support, Non-U.S. Gov't Veleiro, A.S. Nevado, M.V. Monteserín, M.C. Burton, G. Syntheses of 21-hydroxy-11,19-oxidopregn-4-ene-3,20-dione and 21-hydroxy-6,19-oxidopregn-4-ene-3,20-dione |
| topic_facet |
21-hydroxylation oxido-bridged pregnanes 21 hydroxy 11,19 oxidopregn 4 ene 3,20 dione 21 hydroxy 6,19 oxidopregn 4 ene 3,20 dione 21-hydroxy-11,19-oxidopregn-4-ene-3,20-dione 21-hydroxy-6,19-oxidopregn-4-ene-3,20-dione aldosterone drug derivative progesterone 21 hydroxy 11,19 oxidopregn 4 ene 3,20 dione 21 hydroxy 6,19 oxidopregn 4 ene 3,20 dione deoxycorticosterone mineralocorticoid receptor unclassified drug acetylation article chemical structure chemistry hydroxylation oxidation reduction reaction synthesis drug structure drug synthesis steroidogenesis Acetylation Aldosterone Hydroxylation Molecular Structure Oxidation-Reduction Progesterone Support, Non-U.S. Gov't |
| description |
The 21-hydroxy analogues of 11,19-oxidoprogesterone and 6,19-oxidoprogesterone have been synthesized from readily available materials. Hydroxylation at C-21 was effected with iodosobenzene (from phenyliodosodiacetate and methanolic potassium hydroxide) on a 20-ketopregnane. For the 11,19-oxido derivative, the hydroxylation was carried out on a precursor containing the oxido-bridge. This approach was not adequate for the 6,19-oxido steroid due to the very low yields encountered; hence in the latter case the order of introduction of the C-21 functionality and the oxido-bridge was reversed. © 1995. |
| format |
JOUR |
| author |
Veleiro, A.S. Nevado, M.V. Monteserín, M.C. Burton, G. |
| author_facet |
Veleiro, A.S. Nevado, M.V. Monteserín, M.C. Burton, G. |
| author_sort |
Veleiro, A.S. |
| title |
Syntheses of 21-hydroxy-11,19-oxidopregn-4-ene-3,20-dione and 21-hydroxy-6,19-oxidopregn-4-ene-3,20-dione |
| title_short |
Syntheses of 21-hydroxy-11,19-oxidopregn-4-ene-3,20-dione and 21-hydroxy-6,19-oxidopregn-4-ene-3,20-dione |
| title_full |
Syntheses of 21-hydroxy-11,19-oxidopregn-4-ene-3,20-dione and 21-hydroxy-6,19-oxidopregn-4-ene-3,20-dione |
| title_fullStr |
Syntheses of 21-hydroxy-11,19-oxidopregn-4-ene-3,20-dione and 21-hydroxy-6,19-oxidopregn-4-ene-3,20-dione |
| title_full_unstemmed |
Syntheses of 21-hydroxy-11,19-oxidopregn-4-ene-3,20-dione and 21-hydroxy-6,19-oxidopregn-4-ene-3,20-dione |
| title_sort |
syntheses of 21-hydroxy-11,19-oxidopregn-4-ene-3,20-dione and 21-hydroxy-6,19-oxidopregn-4-ene-3,20-dione |
| url |
http://hdl.handle.net/20.500.12110/paper_0039128X_v60_n3_p268_Veleiro |
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