A novel and regiospecific route to 5-acyluridines via an amide .ALPHA.-anion derived from 5,6-dihydrouridine.

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Upon lithiation with LDA, 2', 3'-O-isopropylidene-5'-O-methoxymethyl-5, 6-dihydrouridine has been shown to serve as an "amide α-anion". Thus, acylation of the resulting dianion took place regiospecifically at the C-5 position. The subsequent phenylselenenylation and oxidative elimination afforded 5-acyluridines.

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