• Title/Summary/Keyword: Ring-closing metathesis

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Synthesis of 4′$\alpha$-C Methyl Branched Novel Adenine and Uracil Carbocyclic Nucleosides Using Ring-Closing Metathesis (Ring-Closing Metathesis 반응을 이용한 새로운 4-메칠 아데닌 및 유라실 카보사이클릭 뉴크레오사이드의 합성)

  • 홍준희
    • YAKHAK HOEJI
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    • v.47 no.5
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    • pp.271-275
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    • 2003
  • Easy and efficient synthetic route of novel 4'-C methyl branched carbocyclic nucleosides is described. The installation of alkyl and aryl groups at 4'-position of carbocyclic nucleosides were successfully made via sequential [3,3]-sigmatropic rearrangement and ring-closing metathesis (RCM) starting from simple ketones such as acetol. Adenine and uracil were coupled via Pd(0) catalyzed reaction, followed by desilylation to give novel compounds 13 and 14, respectively.

Synthesis of Novel Mercaptophenyl Carbocyclic C-Nucleoside Analogue Using Sequential [3,3]-Sigmatropic Rearrangement and Ring-closing Metathesis

  • Li, Hua;Hong, Joon-Hee
    • Bulletin of the Korean Chemical Society
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    • v.29 no.4
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    • pp.847-850
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    • 2008
  • Novel mercaptophenyl carbocyclic C-nucleoside analogue was synthesized via a cyclopentenol intermediate 10, which was prepared using a sequential [3,3]-sigmatropic rearrangement and ring-closing metathesis (RCM). Friedel-Crafts alkylation was then used to couple the thiophenol.

Synthesis of 4'α-C Phenyl-Branched Carbocyclic Nucleoside Using Ring-Closing Metathesis

  • Hong, Joon-Hee;Ko, Ok-Hyun
    • Bulletin of the Korean Chemical Society
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    • v.24 no.9
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    • pp.1289-1292
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    • 2003
  • An efficient synthetic route for preparing novel $4'{\alpha}$-C phenyl branched carbocyclic nucleoside is described. The installation of phenyl group at the $4'$-position of carbocyclic nucleoside was successfully accomplished via a sequential [3,3]-sigmatropic rearrangement and ring-closing metathesis (RCM) beginning from simple ketone such as 2-hydroxy acetophenone.

Synthesis of 2'-Methyl and 4'-Hydroxy Branched Novel Carbocyclic Nucleosides (2'-메칠 및 4'-하이드록시 측쇄를 가진 새로운 카보사이클릭 뉴크레오사이드의 합성)

  • 홍준희;고옥현
    • YAKHAK HOEJI
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    • v.47 no.6
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    • pp.417-421
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    • 2003
  • This paper describes a synthetic route to novel 2'-methyl and 4'-hydroxy carbocyclic nucleosides. The methyl group was successfully installed by carbonyl addition reaction of isopropenyl magnesium bromide followed by ring-closing metathesis and the hydroxy group was directly introduced from carbohydrate chiral template "D-lactose".ose".uot;.

An Efficient Synthesis of 4'-Vinylated Carbocyclic Nucleoside Analogues via Two Directional Ring-closing Metathesis

  • Li, Hua;Hong, Joon-Hee
    • Bulletin of the Korean Chemical Society
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    • v.29 no.5
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    • pp.993-997
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    • 2008
  • Two directional ring-closing metathesis (RCM) was applied successfully to the synthesis of 4'-vinylated carbocyclic nucleoside analogues from the trivinyl intermediate 12, which was readily made using a sequential Claisen rearrangement and ring-closing metathesis (RCM) starting from Weinreb amide 5. An antiviral evaluation of the synthesized compounds against various viruses such as HIV, HSV-1, HSV-2 and HCMV revealed that the guanine analogue 20 have moderate anti-HIV activity in the MT-4 cell line ($EC_{50}$ = 10.2 $\mu$ M).