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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 30, Number 9
BKCSDE 30(9)
September 20, 2009 

Synthesis of Neplanocin A Analog with 2′-“up”-C-Methyl Substituent as Potential Anti-HCV Agent
Hyung Rock Lee, Jin Ah Kang, Ah Young Park, Won Hee Kim, Pusoon Chun, Jungsu Kim, Jin Ah Kim, Boeun Lee, Lak Shin Jeong, Hyung Ryong Moon*
2′-β-C-Methylneplanocin A, 2-β-C-Methylribonolactone, Chemoselective, HCV, PDC oxidation
2′-β-C-Methylneplanocin A (3) was synthesized via 2-β-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 SN2 product 27 along with an SN2′ product 28.
2043 - 2050
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