Conformationally locked uridine in the ‘southern’ conformation, which could be an
important precursor for corresponding nucleotides, was stereoselectively synthesized.
Southern uridine nucleotides are expected to be full agonists for the P2Y6 receptor. Poor diastereoselectivity in the osmium-mediated dihydroxylation on the
allyl amine was overcome by introduction of an allyl azide on which osmium medium
hydroxylation, and subsequent cyclization yielded 6-oxabicyclo[3.2.0]heptane in a
9:1 ratio. High regioselectivity between the 2′- and 3′-hydroxyl groups in the intramolecular
O-alkylation and construction of uracil moiety from the azido group provided the final
target, a southern 2′-benzoylated uridine derivative.
nucleoside - nucleotide - carbohydrate - carbocycle - stereoselective synthesis
