Synthesis of carbocyclic analogs of 2',3'-dideoxysangivamycin, 2',3'-dideoxytoyocamycin, and 2',3'-dideoxytriciribine.
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.
Gudmundsson
K S
KS
Division of Chemistry, Glaxo Wellcome Inc, Research Triangle Park, NC 27709, USA.
Wang
Z
Z
Daluge
S M
SM
Feldman
P L
PL
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
D000998:Antiviral Agents; D003853:Deoxyribonucleosides; D011741:Pyrimidine Nucleosides; D012263:Ribonucleosides; C005699:sangivamycin; C023764:triciribine; D014127:Toyocamycin