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Synthesis 2023; 55(04): 657-662
DOI: 10.1055/a-1941-1437
paper

Convenient Synthesis of Ellagic Acid from Methyl Gallate and SARS-CoV-2 3CLpro Antiviral Activity

Francesc Navarro
a   Laboratori de Química Farmacèutica, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII, 27-31, 08028 Barcelona, Spain
,
Salha Hamri
a   Laboratori de Química Farmacèutica, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII, 27-31, 08028 Barcelona, Spain
,
Rosa Reches
a   Laboratori de Química Farmacèutica, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII, 27-31, 08028 Barcelona, Spain
,
Miquel Viñas
a   Laboratori de Química Farmacèutica, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII, 27-31, 08028 Barcelona, Spain
,
Daniel Jahani
a   Laboratori de Química Farmacèutica, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII, 27-31, 08028 Barcelona, Spain
,
Jaume Ginard
a   Laboratori de Química Farmacèutica, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII, 27-31, 08028 Barcelona, Spain
,
Josep Vilardell
a   Laboratori de Química Farmacèutica, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII, 27-31, 08028 Barcelona, Spain
,
Olga Abián
b   Dpt. Bioquímica/IUI BIFI, Mariano-Esquillor, Edificio I+D Campus Río Ebro, Universidad de Zaragoza, 50018 Zaragoza, Spain
,
M. Dolors Pujol  ∗
a   Laboratori de Química Farmacèutica, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII, 27-31, 08028 Barcelona, Spain
› Author AffiliationsFinancial support from Servier Laboratories is gratefully acknowledged.
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Abstract

A practical synthesis of ellagic acid has been achieved from methyl gallate by a proposed synthetic route of five steps, consisting of ketal protection, regioselective bromination, bis-lactonization, C–C bond formation between the aromatic rings of the galloyl groups, and ketal deprotection, in 38% overall yield. Ellagic acid showed a slight inhibitory activity against SARS-CoV-2 3CLpro.

Keywords

ellagic acid - gallic acid - polyphenols - reductive coupling - ketals

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1941-1437.
  • Supporting Information


Publication History

Received: 28 July 2022

Accepted after revision: 12 September 2022

Accepted Manuscript online:
12 September 2022

Article published online:
18 October 2022

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