title: Synthesis of carbocyclic analogs of 2',3'-dideoxysangivamycin, 2',3'-dideoxytoyocamycin, and 2',3'-dideoxytriciribine.
abstract: Syntheses and antiviral activity of new carbocyclic analogs of 2', 3'-dideoxysangivamycin, 2',3'-dideoxytoyocamycin and 2',3'-dideoxytriciribine is described. The key intermediate, carbocyclic 4-chloro-5-iodopyrrolopyrimidine. was synthesized in good yield via a novel iodination method using I2 and CF3COOAg. This carbocyclic 4-chloro-5-iodopyrrolopyrimidine then allowed for a concise synthesis of the desired 4,5-disubstituted carbocyclic nucleosides.
authors.affiliation: Division of Chemistry, Glaxo Wellcome Inc, Research Triangle Park, NC 27709, USA.
authors.forename: K S
authors.initials: KS
authors.lastname: Gudmundsson
authors.forename: Z
authors.initials: Z
authors.lastname: Wang
authors.forename: S M
authors.initials: SM
authors.lastname: Daluge
authors.forename: P L
authors.initials: PL
authors.lastname: Feldman
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D003853:Deoxyribonucleosides / Q000378:metabolism / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis*; D012263:Ribonucleosides / Q000138:chemical synthesis*; D014127:Toyocamycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D000998:Antiviral Agents; D003853:Deoxyribonucleosides; D011741:Pyrimidine Nucleosides; D012263:Ribonucleosides; C005699:sangivamycin; C023764:triciribine; D014127:Toyocamycin