Ni‐Catalyzed Cross‐Coupling of 2‐Iodoglycals and 2‐Iodoribals with Grignard Reagents: A Route to 2‐<i>C</i>‐Glycosides and 2’‐<i>C</i>‐Nucleosides
Peter Polák, Janine Cossy
Abstract
The synthesis of 2-C-glycals and 2-C-ribals was achieved in good yields using a nickel-catalyzed cross-coupling between 2-iodoglycals and 2-iodoribal respectively and Grignard reagents. The prepared 2-C-glycals and ribals were then transformed into 2-C-2-deoxyglycosides, 2-C-diglycosides and 2'-C-2'-deoxynucleosides. The developed method was applied to the synthesis of a 2-chloroadenine 2'-deoxyribonucleoside - a structural analogue of cladribine (Mavenclad®, Leustatin®) and clofarabine (Clolar®, Evoltra®), two compounds used in the treatment of relapsing-remitting multiple sclerosis and hairy cell leukemia.
Topics & Concepts
CladribineDeoxyribonucleosideChemistryReagentDeoxyribonucleosidesCatalysisCombinatorial chemistryStereochemistryGrignard reactionOrganic chemistryEnzymeBiologyGeneticsCarbohydrate Chemistry and SynthesisSynthesis of Organic CompoundsHIV/AIDS drug development and treatment