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The First Total Syntheses of the Diglycosides Virgaureoside A, of Solidago virgaurea L., and its Analogue iso-Virgaureoside A

[ Vol. 14 , Issue. 3 ]

Author(s):

Elena V. Stepanova, Marina O. Nagornaya, Maxim L. Belyanin and Victor D. Filimonov   Pages 394 - 397 ( 4 )

Abstract:


Background: Virgaureoside A is a component of Solidago virgaurea L. (Goldenrod ordinary) which is a well-known remedy in folk Chinese medicine. However, the isolation and, consequently, pharmacological testing of this diglycoside is difficult due to its low content.

Objective: To perform the first total synthesis of the diglycoside Virgaureoside A and apply the developed synthetic approach to the synthesis of analogues compound, iso-Virgareoside A, thus allowing the acquisition of these diglycosides in any desired quantity and thereby permit an assessment of their potential biological properties.

Results: The first syntheses of Virgaureoside A [2-(β-D-glucopyranosyloxy)benzyl 2-(β-D-glucopyranosyloxy) benzoate], a diglycoside of the Solidago virgaurea L. plant, and iso-Virgaureoside A [2-(β-D-glucopyranosyloxy) benzyl 4-(β-D-glucopyranosyloxy)benzoate], which is not found in nature and has not been described in the literature, have been accomplished. The key step involved selective acid catalyzed cleavage of acetyl esters in the presence of a substituted benzoyl ester and two glycosidic linkages.

Conclusion: The desired products Virgaureoside A and iso-Virgaureoside A were synthesized in four steps in 5.6% and 3.0% overall yield, starting from ethyl 2-hydroxybenzoate and ethyl 4-hydroxybenzoate, respectively.

Keywords:

Diglycosides, virgaureoside A, o-hydroxybenzyl salicylate, Solidago virgaurea L.

Affiliation:

Department of Biotechnology and Organic Chemistry, National Research Tomsk Polytechnic University, 30 Lenin Avenue, Tomsk, 634050

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