Abstract
A novel efficient method for the synthesis of 3‘-β-branched uridines starting from uridine was developed, in which a SmI2-promoted intramolecular Reformatsky-type reaction was effectively used. 5‘-O-(Bromoacetyl)-3‘-ketouridine derivatives 12, 26, and 27 were synthesized from uridine and were subjected to an intramolecular Reformatsky-type reaction. When 12, 26, and 27 were treated with 2.0 equiv of SmI2 in THF at −78 °C, intramolecular carbon−carbon bond formation at the 3‘-β-position proceeded smoothly to give the corresponding 3‘,5‘-lactones 14, 28, and 29 in high yields, respectively. Treatment of 28 with NH3/MeOH gave the 3‘-β-branched uridine derivative 32 quantitatively, which was then deprotected to give 3‘-C-(carbamoylmethyl)uridine (33).
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