A NOVEL AND REGIOSPECIFIC ROUTE TO 5-ACYLURIDINES VIA AN AMIDE α-ANION DERIVED FROM 5, 6-DIHYDROURIDINE

Abstract

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.