Enantiomeric synthesis of carbocyclic analogs ofD- andL-6-azapyrimidine ribonucleosides

Abstract

An effective and practical synthesis of carbocyclic D- and L-6-azapyrimidine nucleosides (3–8) was described. Starting from D-ribose, a new efficient methodology for the synthesis of L-2,3-O-cyclohexylidene-4-cyclopentenone (23) was developed via a ring-closing metathesis, which was applied for the synthesis of L-cyclopentyl-6-azapyrimidine nucleosides (6–8). The regiospecific introduction of 6-azauracil on the carbocyclic moiety (9 and 25) was also achieved by masking its N3position with a 4-methylthio group.Key words: carbocyclic nucleosides, 6-azapyrimidine nucleosides, enantiomeric synthesis.