• Title/Summary/Keyword: Felkin-Anh model

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Stereoselective Synthesis and Antiviral Activity of Novel 4′(α)-Hydroxymethyl and 6′(α)-Methyl Dually Branched Carbocyclic Nucleosides

  • Kim, Jin-Woo;Choi, Bo-Gil;Hong, Joon-Hee
    • Bulletin of the Korean Chemical Society
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    • v.25 no.12
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    • pp.1812-1816
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    • 2004
  • The stereoselective synthesis 4′,6′-dually branched carbocyclic nucleosides was accomplished in this study. The introduction of a methyl group in the 6′$({\alpha})$-position was accomplished by Felkin-Anh controlled alkylation. The construction of the required 4′$({\alpha})$-quaternary carbon was carried out using a [3,3]-sigmatropic rearrangement. Bis-vinyl 6 was successfully cyclized using a Grubbs' catalyst II. The natural bases (adenine, cytosine) were efficiently coupled using a Pd(0) catalyst. When the synthesized compounds were examined for their activity against several viruses such as the HIV-1, HSV-1, HSV-2 and HCMV, the cytosine analogue 13 exhibited good antiviral activity against the HCMV.

Synthesis and Antiviral Activity of Novel 4',5'-Branched Pyrimidine Nucleosides (4',5'-측쇄를 가진 새로운 피리미딘 뉴크레오사이드의 합성 및 항바이러스 약효검색)

  • Kim Aihong;Kooh Dae-Ho;Ko Ok Hyun;Hong Joon Hee
    • YAKHAK HOEJI
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    • v.49 no.1
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    • pp.20-24
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    • 2005
  • The synthesis of 4',5'-doubly branched carbocyclic nucleosides was accomplished in this study. The selective methylation in the 5'-position was made by Felkin-Anh controlled Grignard addition. The construction of the required 4'-quaternary carbon was carried out by using a [3,3]-sigmatropic rearrangement. Bis-vinyl 6 was successfully cyclized using a Grubbs' catalyst II. The natural pyrimidine bases (cytosine, uracil, thymine) were efficiently coupled using a Pd(0) catalyst. When the synthesized compounds were examined for their activity against several viruses such as the HIV-1, HSV-1, HSV-2 and HCMV, the cytosine analogue 13 exhibited weak antiviral activity against the HCMV.