Bulletin of the Korean Chemical Society

  • 제28권9호
  • /
  • Pages.1545-1548
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  • 2007
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Efficient Construction of Quaternary Carbon: Stereocontrolled Synthesis of Novel Abacavir Analogue

  • Kim, Ai-Hong (BK-21 Project Team, College of Pharmacy, Chosun University) ;
  • Hong, Joon-Hee (BK-21 Project Team, College of Pharmacy, Chosun University)
  • 발행 : 2007.09.20
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초록

This paper discusses the racemic and stereoselective synthetic route for novel 4'α -methyl and 6'α -methyl analogues of abacavir. The quaternary carbon at the 4'-position of carbocyclic nucleoside was installed successfully via a Claisen rearrangement. The stereocontrolled construction of a methyl group in the 6'α - position was directed through the Felkin-Anh rule. A Bis-vinyl compound 9 was cyclized successfully using Grubbs' catalyst II to provide a carbocycle nucleus for the target compound. The synthesized compound 15 showed moderate anti-HIV activity (EC50 = 10.67 μM, MT-4 cell lines).

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참고문헌

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피인용 문헌

  1. Enantioselective synthesis of the carbocyclic nucleoside (−)-abacavir vol.10, pp.9, 2012, https://doi.org/10.1039/c2ob06775g
  2. ChemInform Abstract: Efficient Construction of Quaternary Carbon: Stereocontrolled Synthesis of Novel Abacavir Analogue. vol.39, pp.8, 2008, https://doi.org/10.1002/chin.200808204
  3. Synthesis and Anti-HIV-1 Activity of Carbocyclic Versions of Stavudine Analogues Using a Ring-closing Metathesis vol.29, pp.9, 2007, https://doi.org/10.5012/bkcs.2008.29.9.1723
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  5. Asymmetric Hydroformylation of an Enantiomerically Pure Bicyclic Lactam: Efficient Synthesis of Functionalised Cyclopentylamines vol.16, pp.43, 2007, https://doi.org/10.1002/chem.201002233
  6. A new approach to cyclopentitols using CrCl2 mediated domino reaction and ring closing metathesis. The synthesis of 4a-carba-β-D-arabinofuranose and 4a-carba-β-https://doi.org/10.1016/j.tetasy.2011.04.012