Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis of Neplanocin A Analog with 2′-“up”-C-Methyl Substituent as Potential Anti-HCV Agent

  • Lee, Hyung-Rock (Laboratory of Medicinal Chemistry, College of Pharmacy and Research Institute for Drug Development, Pusan National University) ;
  • Kang, Jin-Ah (Laboratory of Medicinal Chemistry, College of Pharmacy and Research Institute for Drug Development, Pusan National University) ;
  • Park, Ah-Young (Laboratory of Medicinal Chemistry, College of Pharmacy and Research Institute for Drug Development, Pusan National University) ;
  • Kim, Won-Hee (Laboratory of Medicinal Chemistry, College of Pharmacy and Research Institute for Drug Development, Pusan National University) ;
  • Chun, Pu-Soon (Laboratory of Medicinal Chemistry, College of Pharmacy and Research Institute for Drug Development, Pusan National University) ;
  • Kim, Jung-Su (Laboratory of Medicinal Chemistry, College of Pharmacy and Research Institute for Drug Development, Pusan National University) ;
  • Kim, Jin-Ah (Laboratory of Medicinal Chemistry, College of Pharmacy and Research Institute for Drug Development, Pusan National University) ;
  • Lee, Bo-Eun (College of Pharmacy, Seoul National University) ;
  • Jeong, Lak-Shin (Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University) ;
  • Moon, Hyung-Ryong (Laboratory of Medicinal Chemistry, College of Pharmacy and Research Institute for Drug Development, Pusan National University)
  • Published : 2009.09.20
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Abstract

2′-$\beta$-C-Methylneplanocin A (3) was synthesized via 2-$\beta$-C-methylribonolactone, prepared by a modified Whistler and BeMiller’s method developed by our laboratory, as potential anti-HCV agent. Reduction of 14 with Dibal-H afforded 26 in a good yield with a trace of 25, whereas a Luche reduction gave 26/25 = 4/1 mixture. Several attempts were made to chemoselectively remove TBS group in the presence of TBDPS group and treatment with both PPTS and TsOH showed the best result. Condensation of 26 with 6-chloropurine under Mitsunobu conditions produced an $S_N$2 product 27 along with an $S_N$2′ product 28.

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References

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