title: Synthesis of cyclopentanyl carbocyclic 5-fluorocytosine ((-)-5-fluorocarbodine) using a facially selective hydrogenation approach.
abstract: An efficient synthetic route to biologically relevant (-)-5-fluorocarbodine 6 was developed. Direct coupling of N(6)-protected 5-fluorouracil 15 with cyclopentenyl intermediate 13, followed by formation of a macrocycle between the base and the carbocyclic sugar moiety, via ring-closing metathesis, allowed for a facial selective hydrogenation of the sugar double bond to give, exclusively, the desired 4'-β stereoisomer.
authors.affiliation: Center for AIDS Research, Laboratory of Biochemical Pharmacology, Department of Pediatrics, Emory University School of Medicine, and Veterans Affairs Medical Center, Decatur, Georgia 30033, USA.
authors.forename: Jong Hyun
authors.initials: JH
authors.lastname: Cho
authors.forename: Franck
authors.initials: F
authors.lastname: Amblard
authors.forename: Steven J
authors.initials: SJ
authors.lastname: Coats
authors.forename: Raymond F
authors.initials: RF
authors.lastname: Schinazi
mesh_terms: D003500:Cyclization; D003517:Cyclopentanes / Q000737:chemistry*; D003562:Cytidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D005437:Flucytosine / Q000138:chemical synthesis* / Q000737:chemistry; D005472:Fluorouracil / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D006865:Hydrogenation; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D003517:Cyclopentanes; D003562:Cytidine; C033357:carbodine; D005437:Flucytosine; D005472:Fluorouracil