Piperonal as Starting Material for the Regiospecific and Stereoselective Synthesis of E and Z Isomers of 3-Methyl-2-hexenedioic acid-1-methyl ester

Sergio Pinheiro Departamento de Química Orgânica, Instituto de Química, Universidade Federal Fluminense, Niterói, RJ, Brazil

Rosane N. Castro Núcleo de Presquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, Centro de Ciências da Saúde Bloco H, 21941, Ilha do Fundão, Rio de Janeiro, RJ, Brazil

Maria F. G. Fernandes Núcleo de Presquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, Centro de Ciências da Saúde Bloco H, 21941, Ilha do Fundão, Rio de Janeiro, RJ, Brazil

Paulo R. R. Costa Núcleo de Presquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, Centro de Ciências da Saúde Bloco H, 21941, Ilha do Fundão, Rio de Janeiro, RJ, Brazil

Abstract

A short synthesis of γ-lactone 5 was developed starting from the easily available piperonal 1. The key step in this approach was an ozonation of the aromatic ring of 2. Compound 5 led stereoselectively to 6 or 7 by a β-elimination reaction under thermodynamic or kinetic conditions.

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Piperonal as Starting Material for the Regiospecific and Stereoselective Synthesis of E and Z Isomers of 3-Methyl-2-hexenedioic acid-1-methyl ester

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Piperonal as Starting Material for the Regiospecific and Stereoselective Synthesis of E and Z Isomers of 3-Methyl-2-hexenedioic acid-1-methyl ester

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