title: Synthesis of racemic and enantiomeric 3-pyrrolidinyl derivatives of purine and pyrimidine nucleobases.
abstract: The present work relates to the synthesis of pyrrolidine nucleoside analogs. Starting from malic acid, we have elaborated a high-yield synthesis of racemic and enantiomeric N-protected 3-pyrrolidinols and their O-mesyl derivatives as key compounds for alkylations of purine and pyrimidine nucleobases. On varying base and solvent, we have found conditions providing both satisfactory N-/O-regioisomeric ratio and acceptable yield for pyrimidine compounds.
authors.affiliation: Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Praha 6, Czech Republic.
authors.forename: Petr
authors.initials: P
authors.lastname: Kocalka
authors.forename: Radek
authors.initials: R
authors.lastname: Pohl
authors.forename: Dominik
authors.initials: D
authors.lastname: Rejman
authors.forename: Ivan
authors.initials: I
authors.lastname: Rosenberg
mesh_terms: D000970:Antineoplastic Agents / Q000494:pharmacology; D000998:Antiviral Agents / Q000494:pharmacology; D002626:Chemistry, Pharmaceutical / Q000379:methods; D009682:Magnetic Resonance Spectroscopy; D008293:Malates / Q000737:chemistry; D013058:Mass Spectrometry; D008956:Models, Chemical; D009690:Nucleic Acid Conformation; D009705:Nucleosides / Q000737:chemistry*; D009711:Nucleotides / Q000737:chemistry; D011684:Purine Nucleosides / Q000737:chemistry; D011687:Purines / Q000737:chemistry*; D011741:Pyrimidine Nucleosides / Q000737:chemistry; D011743:Pyrimidines / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000970:Antineoplastic Agents; D000998:Antiviral Agents; D008293:Malates; D009705:Nucleosides; D009711:Nucleotides; D011684:Purine Nucleosides; D011687:Purines; D011741:Pyrimidine Nucleosides; D011743:Pyrimidines; D012997:Solvents; C030298:malic acid