title: Conformationally locked bicyclo[4.3.0]nonane carbanucleosides: synthesis and bio-evaluation.
abstract: D-Ribose was converted into 3 novel carbobicyclic nucleosides bearing a bicyclo[4.3.0]nonane framework in 16-19 steps with 5-12% overall yields involving a Wittig olefination and an intramolecular Diels-Alder reaction as the key steps. The present synthesis also provides an efficient entry for chiral hydrindenones. The conformation studies of these carbanucleosides and their bio-evaluation as potential antiviral agents are reported.
authors.affiliation: Department of Chemistry and Center of Novel Functional Molecules, The Chinese University of Hong Kong, Shatin, Hong Kong, China.
authors.forename: Tony K M
authors.initials: TK
authors.lastname: Shing
authors.forename: Anthony W H
authors.initials: AW
authors.lastname: Wong
authors.forename: Huiyan
authors.initials: H
authors.lastname: Li
authors.forename: Z F
authors.initials: ZF
authors.lastname: Liu
authors.forename: Paul K S
authors.initials: PK
authors.lastname: Chan
mesh_terms: D000473:Alkanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002470:Cell Survival / Q000187:drug effects; D002522:Chlorocebus aethiops; D061565:Cycloaddition Reaction; D029822:Enterovirus B, Human / Q000187:drug effects / Q000254:growth & development; D008968:Molecular Conformation; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D012266:Ribose / Q000737:chemistry*; D013237:Stereoisomerism; D014709:Vero Cells
chemical_list: D000473:Alkanes; D000998:Antiviral Agents; D001643:Bridged Bicyclo Compounds; D009705:Nucleosides; D012266:Ribose; C017573:nonane