ChemInform Abstract: Synthesis of ara-Cadeguomycin: 2-Amino-3,4-dihydro-4-oxo-7-(β-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic Acid.

ChemInform Abstract

Glycosylation of the base (I) with the D-arabinofuranosyl Chloride (II) followed by acetylamination yields an anomeric mixture of (IVa) and (IVb). Debenzylation of (IVb) followed by acetylation and bromination affords the bromide (VI). The next steps include the conversion of the methyl group to the corresponding acid [via bromide, alcohol, aldehyde and acid bromide] and its debromination to give (VII). Deprotection of (VII) yields the title compound (VIII).