Stereocontrolled syntheses of carbocyclic C-nucleosides and related compounds.
Carbocyclic 9-deazapurine nucleosides (1-4), a spiranic pyrimidone carbocyclic compound (5), and an unusual carbocyclic isonucleoside (6) were prepared as enantiomerically pure compounds via the key intermediates 10 and 21 from 1,4-gamma-ribonolactone. The key intermediate 10 was prepared by stereoselective reduction with Bu3SnH and then converted to carbocyclic C-ribonucleosides 1, 3, and 4. 2',3'-Didehydro-2',3'-dideoxycarbocyclic 9-deazainosine (2) was prepared from a 2',3'-dimesylate 17 by treatment with Li2Te followed by an acidic deprotection. The key bicyclic intermediate 21 was prepared from a diol 20 by an intramolecular cyclization using CHI3-Ph3P-imidazole and converted to the spiranic compound 5 and an olefinic nucleoside 6 by the construction of the heterocyclic moiety followed by deprotection.
Chun
B K
BK
Department of Pharmaceutical and Biomedical Sciences, College of Pharmacy, The University of Georgia, Athens, Georgia 30602, USA.
Song
G Y
GY
Chu
C K
CK
D000970:Antineoplastic Agents / Q000138:chemical synthesis; D000998:Antiviral Agents / Q000138:chemical synthesis; D002478:Cells, Cultured; D015497:HIV-1 / Q000187:drug effects; D006801:Humans; D007288:Inosine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology; D007963:Leukocytes, Mononuclear / Q000821:virology; D009705:Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology
D000970:Antineoplastic Agents; D000998:Antiviral Agents; D009705:Nucleosides; C047906:carbocyclic inosine; D007288:Inosine