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Synthesis of novel Bi-, Tri-, and tetracyclic nucleosides by reaction of a common cyclic enamine derived from TSAO-T with nucleophiles

AuthorsBonache, María-Cruz; Chamorro, Cristina; Cordeiro, Alessandra; Camarasa Rius, María José ; Jimeno, M. Luisa ; San-Félix, Ana
Issue Date2004
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 69 : 8758-8766 (2004)
AbstractWe 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.
Publisher version (URL)http://dx.doi.org/10.1021/jo048706p
Appears in Collections:(CENQUIOR) Artículos
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