| Synthesis of novel Bi-, Tri-, and tetracyclic nucleosides by reaction of a common cyclic enamine derived from TSAO-T with nucleophiles. | |
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MedLine Citation:
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PMID: 15575754 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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María-Cruz Bonache; Cristina Chamorro; Alessandra Cordeiro; María-José Camarasa; María-Luisa Jimeno; Ana San-Félix |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 69 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2004 Dec |
Date Detail:
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Created Date: 2004-12-03 Completed Date: 2005-02-14 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 8758-66 Citation Subset: IM |
Affiliation:
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Instituto de Química Médica, CSIC, Juan de la Cierva 3, 28006 Madrid, Spain. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Amines
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chemical synthesis,
chemistry* Anti-HIV Agents / chemical synthesis* Heterocyclic Compounds with 4 or More Rings / chemical synthesis* Molecular Conformation Nucleosides / chemical synthesis* Spiro Compounds / chemistry* Stereoisomerism Thymidine / analogs & derivatives*, chemistry* |
| Chemical | |
Reg. No./Substance:
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0/Amines; 0/Anti-HIV Agents; 0/Heterocyclic Compounds with 4 or More Rings; 0/Nucleosides; 0/Spiro Compounds; 141781-17-1/(2',5'-bis-O-(tert-butyldimethylsilyl)-beta-ribofuranosyl)-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)thymine; 50-89-5/Thymidine |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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