Journal of the Chemical Society. Chemical communications p. 1319 - 1320 (1991)
Update date:2022-07-30
Topics: Regioselectivity Yield Stereochemistry Chromatography Recrystallization Total synthesis Mass spectrometry (MS) Deprotection TLC (thin-layer chromatography) HPLC (high-performance liquid chromatography) Protecting group Glycosylation Workup Catalysis Reaction Monitoring Aglycone anthraquinone NMR spectroscopy (Nuclear Magnetic Resonance) Solvent system
Allevi, Pietro
Anastasia, Mario
Ciuffreda, Pierangela
Fiecchi, Alberto
Scala, Antonio
et al.
The first synthesis of carminic acid (7β-D-glucopyranosyl-1-methyl-3,5,6,8-tetrahydroxy-9,10-anthraquinone-2-carboxylic acid), was accomplished by direct C-glucosylation of ethyl 3,5,8,9,10-pentamethoxy-1-methylanthracene-2-carboxylate, here synthesized, which affords ethyl 7-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-3,5,8,9,10-pentamethoxy-1-methylanthracene-2-carboxylate and carminic acid by regeneration of the masked functionalities.
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