Branched-chain Sugars. XXIX. Synthesis of Moenuronic Acid (4-<i>C</i>-Methyl-<scp>d</scp>-glucuronic Acid)

Abstract

Abstract Moenuronic acid (4-C-methyl-d-glucuronic acid), a branched-chain sugar component of moenomycin A, was synthesized by the introduction of an axial C-methyl group into methyl 2,3-di-O-benzyl-6-O-trityl-α-d-xylo-hexopyranosid-4-ulose by the reaction with methyllithium, followed by deprotection and platinum-catalyzed oxidation of the C-6 position. Stereoselectivities in a few reactions for the introduction of C-methyl group were examined.