Acyl migration in the Reformatsky reaction of 21-acyloxy-5-pregnen-20-one derivatives with ethyl bromoacetate
Reformatsky reaction of 3β, 21-diacyloxy- and 3β-methoxy-21-acyloxy-5-pregnen-20-one with ethyl bromoacetate yields, through an intramolecular 1,2-acyl migration, 3β, 20ξ-diacyloxy- and 3β-methoxy-20ξ-acyloxy-14α-card-5-enolide respectively. The 20ξ-acyloxy-14α-card-5-enolides were converted into th...
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todo:paper_0039128X_v39_n2_p181_Seldes2023-10-03T14:49:20Z Acyl migration in the Reformatsky reaction of 21-acyloxy-5-pregnen-20-one derivatives with ethyl bromoacetate Seldes, A.M. Gros, E.G. 21 acyloxypregn 5 en 20 one bromoacetic acid ethyl ester theoretical study Acetic Acids Acylation Hydrocarbons, Brominated Pregnenes Support, Non-U.S. Gov't Reformatsky reaction of 3β, 21-diacyloxy- and 3β-methoxy-21-acyloxy-5-pregnen-20-one with ethyl bromoacetate yields, through an intramolecular 1,2-acyl migration, 3β, 20ξ-diacyloxy- and 3β-methoxy-20ξ-acyloxy-14α-card-5-enolide respectively. The 20ξ-acyloxy-14α-card-5-enolides were converted into the respective 20ξ-hydroxy-14α-card-5-enolides and the 14α-carda-5,20(22)-dienolides. Experimental support to the proposed intramolecular 1,2-acyl migration is provided by the use of labelled compounds. © 1982. Fil:Seldes, A.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Gros, E.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_v39_n2_p181_Seldes |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
21 acyloxypregn 5 en 20 one bromoacetic acid ethyl ester theoretical study Acetic Acids Acylation Hydrocarbons, Brominated Pregnenes Support, Non-U.S. Gov't |
| spellingShingle |
21 acyloxypregn 5 en 20 one bromoacetic acid ethyl ester theoretical study Acetic Acids Acylation Hydrocarbons, Brominated Pregnenes Support, Non-U.S. Gov't Seldes, A.M. Gros, E.G. Acyl migration in the Reformatsky reaction of 21-acyloxy-5-pregnen-20-one derivatives with ethyl bromoacetate |
| topic_facet |
21 acyloxypregn 5 en 20 one bromoacetic acid ethyl ester theoretical study Acetic Acids Acylation Hydrocarbons, Brominated Pregnenes Support, Non-U.S. Gov't |
| description |
Reformatsky reaction of 3β, 21-diacyloxy- and 3β-methoxy-21-acyloxy-5-pregnen-20-one with ethyl bromoacetate yields, through an intramolecular 1,2-acyl migration, 3β, 20ξ-diacyloxy- and 3β-methoxy-20ξ-acyloxy-14α-card-5-enolide respectively. The 20ξ-acyloxy-14α-card-5-enolides were converted into the respective 20ξ-hydroxy-14α-card-5-enolides and the 14α-carda-5,20(22)-dienolides. Experimental support to the proposed intramolecular 1,2-acyl migration is provided by the use of labelled compounds. © 1982. |
| format |
JOUR |
| author |
Seldes, A.M. Gros, E.G. |
| author_facet |
Seldes, A.M. Gros, E.G. |
| author_sort |
Seldes, A.M. |
| title |
Acyl migration in the Reformatsky reaction of 21-acyloxy-5-pregnen-20-one derivatives with ethyl bromoacetate |
| title_short |
Acyl migration in the Reformatsky reaction of 21-acyloxy-5-pregnen-20-one derivatives with ethyl bromoacetate |
| title_full |
Acyl migration in the Reformatsky reaction of 21-acyloxy-5-pregnen-20-one derivatives with ethyl bromoacetate |
| title_fullStr |
Acyl migration in the Reformatsky reaction of 21-acyloxy-5-pregnen-20-one derivatives with ethyl bromoacetate |
| title_full_unstemmed |
Acyl migration in the Reformatsky reaction of 21-acyloxy-5-pregnen-20-one derivatives with ethyl bromoacetate |
| title_sort |
acyl migration in the reformatsky reaction of 21-acyloxy-5-pregnen-20-one derivatives with ethyl bromoacetate |
| url |
http://hdl.handle.net/20.500.12110/paper_0039128X_v39_n2_p181_Seldes |
| work_keys_str_mv |
AT seldesam acylmigrationinthereformatskyreactionof21acyloxy5pregnen20onederivativeswithethylbromoacetate AT groseg acylmigrationinthereformatskyreactionof21acyloxy5pregnen20onederivativeswithethylbromoacetate |
| _version_ |
1782028759229005824 |