Synthesis of uracil polyoxin C from uridine

Abstract

An improved procedure is reported for the asymmetric synthesis of uracil polyoxin C (UPOC) from 2',3'-O-isopropylideneuridine-5'-aldehyde. The methodology described here is based on the highly diastereocontrolled formation of 1-(β-D-allofuranosyl)uracil and its facile conversion into the corresponding 2,5'-O-cyclouridine derivative, a key step for the stereocontrolled formation of the terminal α-amino acid of UPOC.