1998 nucleic acids

nucleic acidsU 0700

09 - 220Synthesis of (1R,2R,4S,5R)-2,4-Dihydroxy-5-hydroxymethylcyclopentylamine and Its Conversion to an Analogueof Aristeromycin. — The nucleoside (X), an isomer of the antibioticaristeromycin, is synthesized from the D-glucose derivative (I). Key feature isthe synthesis of the aminocyclopentane (V) via N-benzyl nitrone cycloadditionto the masked aldehyde (II) and reductive elimination of the tosyl group withconcomitant cleavage of the isoxazolidine ring. — (ROY, A.; PATRA, R.;ACHARI, B.; MANDAL, S. B.; Synlett (1997) 11, 1237-1238; Indian Inst.Chem. Biol., Jadavpur, Calcutta 700 032, India; EN)

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