The first synthesis of carminic acid (7-beta-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-beta-D-glucopyranosyl)-3,5,8,9,10- pentamethoxyl-1-methylanthracene-2-carboxylate and carminic acid by regeneration of the masked functionalities.
The first total synthesis of carminic acid / P. Allevi, M. Anastasia, P. Ciuffreda, A. Fiecchi, A. Scala, S. Bingham, M. Muir, J. Tyman. - In: JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL COMMUNICATIONS. - ISSN 0022-4936. - :18(1991), pp. 1319-1320.
The first total synthesis of carminic acid
P. AlleviPrimo
;M. AnastasiaSecondo
;P. Ciuffreda;
1991
Abstract
The first synthesis of carminic acid (7-beta-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-beta-D-glucopyranosyl)-3,5,8,9,10- pentamethoxyl-1-methylanthracene-2-carboxylate and carminic acid by regeneration of the masked functionalities.
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