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

Francesc Navarro; Salha Hamri; Rosa Reches; Miquel Viñas; Daniel Jahani; Jaume Ginard; Josep Vilardell; Olga Abián; M. Dolors Pujol

doi:10.1055/a-1941-1437

Synthesis, Inhaltsverzeichnis

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

^aLaboratori de Química Farmacèutica, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII, 27-31, 08028 Barcelona, Spain

,

Salha Hamri

^aLaboratori de Química Farmacèutica, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII, 27-31, 08028 Barcelona, Spain

,

Rosa Reches

^aLaboratori de Química Farmacèutica, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII, 27-31, 08028 Barcelona, Spain

,

Miquel Viñas

^aLaboratori de Química Farmacèutica, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII, 27-31, 08028 Barcelona, Spain

,

Daniel Jahani

^aLaboratori de Química Farmacèutica, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII, 27-31, 08028 Barcelona, Spain

,

Jaume Ginard

^aLaboratori de Química Farmacèutica, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII, 27-31, 08028 Barcelona, Spain

,

Josep Vilardell

^aLaboratori de Química Farmacèutica, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII, 27-31, 08028 Barcelona, Spain

,

Olga Abián

^bDpt. Bioquímica/IUI BIFI, Mariano-Esquillor, Edificio I+D Campus Río Ebro, Universidad de Zaragoza, 50018 Zaragoza, Spain

,

M. Dolors Pujol ∗

^aLaboratori de Química Farmacèutica, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII, 27-31, 08028 Barcelona, Spain

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Abstract

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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

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