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Org Biomol Chem ; 12(46): 9439-45, 2014 Dec 14.
Article in English | MEDLINE | ID: mdl-25325214

ABSTRACT

D-Ribose was converted into 3 novel carbobicyclic nucleosides bearing a bicyclo[4.3.0]nonane framework in 16-19 steps with 5-12% overall yields involving a Wittig olefination and an intramolecular Diels-Alder reaction as the key steps. The present synthesis also provides an efficient entry for chiral hydrindenones. The conformation studies of these carbanucleosides and their bio-evaluation as potential antiviral agents are reported.


Subject(s)
Alkanes/chemical synthesis , Antiviral Agents/chemical synthesis , Bridged Bicyclo Compounds/chemical synthesis , Nucleosides/chemical synthesis , Ribose/chemistry , Alkanes/chemistry , Alkanes/pharmacology , Animals , Antiviral Agents/chemistry , Antiviral Agents/pharmacology , Bridged Bicyclo Compounds/chemistry , Bridged Bicyclo Compounds/pharmacology , Cell Survival/drug effects , Chlorocebus aethiops , Cycloaddition Reaction , Enterovirus B, Human/drug effects , Enterovirus B, Human/growth & development , Molecular Conformation , Nucleosides/chemistry , Nucleosides/pharmacology , Stereoisomerism , Vero Cells
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