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http://dx.doi.org/10.5012/bkcs.2009.30.9.2043

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)
Publication Information
Bulletin of the Korean Chemical Society / v.30, no.9, 2009 , pp. 2043-2050 More about this Journal
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$2′ product 28.
Keywords
2′-$\beta$-C-Methylneplanocin A; 2-$\beta$-C-Methylribonolactone; Chemoselective; HCV; PDC oxidation;
Citations & Related Records
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Times Cited By Web Of Science : 2  (Related Records In Web of Science)
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