Organic Letters · 2006 · 36 citations · 32 references
PharmacyMedicinal ChemistryPharmacologyCombinatorial ChemistryDrug DiscoverySynthetic Medicinal ChemistryAntiviral AgentsAntiviral PharmacologyCombinatorial SynthesisHeterocyclic ChemistryMacrocycle SynthesisStereochemical OptimizationAntiviral Drug DesignAntiviral Structure-activity RelationshipsConfiguration At Chiral CentersGlycopyranose StereochemistryMacrocycle Library SynthesisStereochemistry Of Sugar DerivativesStereocontrolled Library SynthesisStereoselective Sugar Synthesis
A facile synthesis is reported for five-membered iminocyclitols which allows for variation in stereochemistry at all the chiral centers, diverse C1- and N-substitution, and the potential for a three-component combinatorial process. The key step is inversion at the C4 stereocenter (L-lyxo sugar --> D-ribono azasugar). The exo-imino to endo-iminocyclitol process was extended to the D-lyxo and the D- and L-hexose series. Some analogues were found to be more potent than N-butyl DNJ and N-nonyl DNJ in antiviral activity.
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Jack E. Baldwin · Journal of the Chemical Society Chemical Communications · 1976 · 2.2K citations
Nicole Zitzmann, Anand S. Mehta, Sandra Carrouée et al. · Proceedings of the National Academy of Sciences · 1999 · 326 citations