The rapid and facile generation of 4′-carbon radicals
from
oxime imidates of nucleosides via 1,5-hydrogen atom transfer induced
by iminyl radicals was developed. The cyclization of 4′-carbon
radicals with olefins, followed by the hydrolysis of imidate residues,
provided various 2′-O,4′-C- and 3′-O,4′-C-bridged
nucleosides. This operationally simple approach can be applied to
the few-step syntheses of 6′S-methyl-2′-O,4′-C-ethylene-bridged 5-methyluridine
(6′S-Me-ENA-T) and S-constrained
ethyl-bridged 5-methyluridine (S-cEt-T).
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