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KMID : 0043320030260121109
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Archives of Pharmacal Research
2003 Volume.26 No. 12 p.1109 ~ p.1116
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Synthsis and Antiviral Evaluation of Novel 3’-and 4 -Doubly Branched Carbocyclic Nucleosides as Potential Antiviral Agents
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Hong Joon-Hee
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Abstract
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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.
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KEYWORD
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Doubly branched carbocyclic nucleosides, [3, 3]-Sigmatropic rearrangement, Anti-viral agents
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