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Título: | Synthesis of novel Bi-, Tri-, and tetracyclic nucleosides by reaction of a common cyclic enamine derived from TSAO-T with nucleophiles |
Autor: | Bonache, María-Cruz CSIC; Chamorro, Cristina CSIC; Cordeiro, Alessandra CSIC; Camarasa Rius, María José CSIC ORCID; Jimeno, M. Luisa CSIC ORCID; San-Félix, Ana CSIC ORCID | Fecha de publicación: | 2004 | Editor: | American Chemical Society | Citación: | Journal of Organic Chemistry 69 : 8758-8766 (2004) | Resumen: | We report here the efficient regio-and stereoselective synthesis of new polycyclic nucleosides using a common cyclic enamine (7) as the starting material. In fact, the reaction of 7, easily prepared by reaction of 5¢-O-Tosyl TSAO-T under basic nonnucleophilic conditions (potassium carbonate), with different classes of nucleophiles, for example, nitrogen-, oxygen-, sulfur-, and carbon-based nucleophiles, or with amino acids afforded, with total regio-and stereoselectivity, new bi-, tri-, and tetracyclic nucleosides. This straighforward route represents an original and unambiguously regio- and stereoselective pathway to these compounds. Some of these polycyclic nucleosides may be useful intermediates for a second series of reactions that may lead to the generation of structurally new nucleosides. | Versión del editor: | http://dx.doi.org/10.1021/jo048706p | URI: | http://hdl.handle.net/10261/34874 | DOI: | 10.1021/jo048706p | ISSN: | 0022-3263 | ISMN: | 10.1021/jo048706p |
Aparece en las colecciones: | (CENQUIOR) Artículos |
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