Synthesis and antiviral activity of novel 2',4'-doubly branched carbocyclic nucleosides.
A series of 2' and 4'-doubly branched carbocyclic nucleosides 15, 16, 17 and 18 were synthesized starting from simple acyclic ketone derivatives. The required 4'-quatemary carbon was constructed using Claisen rearrangement. In addition, the installation of a methyl group in the 2'-position was accomplished using a Grignard carbonyl addition of isopropenylmagnesium bromide. Bis-vinyl was successfully cyclized using a Grubbs' catalyst II. Natural bases (adenine, cytosine) were efficiently coupled by using Pd(0) catalyst.
Kim
Aihong
A
College of Pharmacy, Chosun University, Kwangju, South Korea.
Hong
Joon Hee
JH
D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D006801:Humans; D007659:Ketones / Q000737:chemistry; D009705:Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology
D000998:Antiviral Agents; D007659:Ketones; D009705:Nucleosides