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Synthsis and Antiviral Evaluation of Novel 3'-and 4 -Doubly Branched Carbocyclic Nucleosides as Potential Antiviral Agents  

Hong, Joon-Hee (College of Pharmacy, Chosun University)
Publication Information
Archives of Pharmacal Research / v.26, no.12, 2003 , pp. 1109-1116 More about this Journal
Abstract
A series of 3'- and 4'-branched carbocyclic nucleosides 25, 26, 27, 28, 29 and 30 were synthesized starting from simple acyclic ketone derivatives. The construction of the required quaternary carbon was made using a [3,3]-sigmatropic rearrangement. In addition, the installation of a methyl group in the 3'-position was accomplished using a Horner-Wadsworth-Emmons (HWE) reaction with triethyl 2-phosphonopropionate. Bis-vinyl was successfully cyclized using a Grubbs' catalyst (Ⅱ). Natural bases (adenine, cytosine, uracil) were efficiently coupled with the use of a Pd(0) catalyst.
Keywords
Doubly branched carbocyclic nucleosides; [3,3]-Sigmatropic rearrangement; Anti-viral agents;
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