, Volume 26, Issue 12, pp 1109-1116

Synthesis and antiviral evaluation of novel 3′- and 4′-doubly branched carbocyclic nucleosides as potential antiviral agents

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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.