Artículo
Bruttomesso, A.C.; Doller, D.; Gros, E.G. "Mechanistic studies of the rearrangements of steroidal 16,17-ketols and syntheses of 20→16-cis-γ-carbolactones" (1999) Bioorganic and Medicinal Chemistry. 7(5):943-947
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Abstract:
Utilization of 17-keto-androstanes as starting materials for the synthesis of α- or β-oriented steroidal 20→16-γ-carbolactones has been explored following two different strategies. A highly efficient, stereospecific protocol has been developed for the β-oriented cis-γ-lactone. A different approach, involving prior attachment of a 3-carbon side chain on C-17 of a 17-oxo-16β-acetoxy-androstane led to the epimeric, α-oriented lactone. The mechanism of the rearrangement of epimeric 16β- or 16α-hydroxy-17-keto-androstanes to 17β-hydroxy-16-keto-androstanes was studied by 13C NMR spectroscopy. The former occurs through a 1,2-sigmatropic H-shift, while the latter is likely to take place by simple enolization-reprotonation. Copyright (C) 1999 Elsevier Science Ltd.
Registro:
| Documento: | Artículo |
| Título: | Mechanistic studies of the rearrangements of steroidal 16,17-ketols and syntheses of 20→16-cis-γ-carbolactones |
| Autor: | Bruttomesso, A.C.; Doller, D.; Gros, E.G. |
| Filiación: | Depto. de Quim. Orgánica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, 1428 Buenos Aires, Argentina 3-Dimensional Pharmaceuticals, 665 Stockton Drive, Exton, PA 19341, United States |
| Palabras clave: | Biosynthesis; Natural products; NMR; Stereospecificity; Steroids and sterols; carbonyl derivative; hydroxyl group; ketol; lactone derivative; steroid; tomatine; article; carbon nuclear magnetic resonance; reaction analysis; synthesis; Androstanols; Lactones; Magnetic Resonance Spectroscopy; Models, Chemical; Models, Molecular; Spironolactone |
| Año: | 1999 |
| Volumen: | 7 |
| Número: | 5 |
| Página de inicio: | 943 |
| Página de fin: | 947 |
| DOI: | http://dx.doi.org/10.1016/S0968-0896(99)00042-5 |
| Título revista: | Bioorganic and Medicinal Chemistry |
| Título revista abreviado: | Bioorg. Med. Chem. |
| ISSN: | 09680896 |
| CODEN: | BMECE |
| CAS: | Androstanols; Lactones; Spironolactone, 52-01-7 |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v7_n5_p943_Bruttomesso |
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Citas:
---------- APA ----------
Bruttomesso, A.C., Doller, D. & Gros, E.G. (1999) . Mechanistic studies of the rearrangements of steroidal 16,17-ketols and syntheses of 20→16-cis-γ-carbolactones. Bioorganic and Medicinal Chemistry, 7(5), 943-947.http://dx.doi.org/10.1016/S0968-0896(99)00042-5
---------- CHICAGO ----------
Bruttomesso, A.C., Doller, D., Gros, E.G. "Mechanistic studies of the rearrangements of steroidal 16,17-ketols and syntheses of 20→16-cis-γ-carbolactones" . Bioorganic and Medicinal Chemistry 7, no. 5 (1999) : 943-947.http://dx.doi.org/10.1016/S0968-0896(99)00042-5
---------- MLA ----------
Bruttomesso, A.C., Doller, D., Gros, E.G. "Mechanistic studies of the rearrangements of steroidal 16,17-ketols and syntheses of 20→16-cis-γ-carbolactones" . Bioorganic and Medicinal Chemistry, vol. 7, no. 5, 1999, pp. 943-947.http://dx.doi.org/10.1016/S0968-0896(99)00042-5
---------- VANCOUVER ----------
Bruttomesso, A.C., Doller, D., Gros, E.G. Mechanistic studies of the rearrangements of steroidal 16,17-ketols and syntheses of 20→16-cis-γ-carbolactones. Bioorg. Med. Chem. 1999;7(5):943-947.http://dx.doi.org/10.1016/S0968-0896(99)00042-5
