Total Synthesis of α-Deamino-3-(β-d-glucopyranosyloxy)kynurenine

α-Deamino-3-(β-d-glucopyranosyloxy)kynurenine, a yellow, fluorescent compound isolated from human lens, was synthesized in 8 steps (10% overall yield) from commercially available 3-methoxy-2-nitrobenzaldehyde. Key events included preparation and glucosylation of methyl 4-(3-hydroxy-2-nitrophenyl)-4-oxobutanoate followed by reduction of the nitro group and deprotection.