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Synthesis method demonstrates regioselective addition of thioglucosides in naphthoquinone derivatives, indicating effective functionalization.
Juglone selectively adds tetra-O-acetyl-1-thio-D-glucopyranose at the 3-position of the naphthoquinone. Acetylation of the 5-OH group of juglone directs the addition of acetylthioglucose to the 2-position. Deacetylation of the addition products with hydrogen chloride in methanol afforded juglone-2- and 3-thioglucosides.
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Polonik et al. (2026) studied this question.
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