Document Detail

Synthesis of novel Bi-, Tri-, and tetracyclic nucleosides by reaction of a common cyclic enamine derived from TSAO-T with nucleophiles.
MedLine Citation:
PMID:  15575754     Owner:  NLM     Status:  MEDLINE    
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.
María-Cruz Bonache; Cristina Chamorro; Alessandra Cordeiro; María-José Camarasa; María-Luisa Jimeno; Ana San-Félix
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  69     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2004 Dec 
Date Detail:
Created Date:  2004-12-03     Completed Date:  2005-02-14     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  8758-66     Citation Subset:  IM    
Instituto de Química Médica, CSIC, Juan de la Cierva 3, 28006 Madrid, Spain.
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MeSH Terms
Amines / 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*
Thymidine / analogs & derivatives*,  chemistry*
Reg. No./Substance:
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

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