Synthesis of Pyrethroids and Jasmonoids through Palladium-Catalyzed Cross-Coupling Reactions

Florencia Parpal; Ana Paula Paullier; Enrique Pandolfi; Viviana Heguaburu

doi:10.1055/a-1736-1749

Synthesis, Table of Contents

Synthesis 2022; 54(11): 2629-2634
DOI: 10.1055/a-1736-1749

paper

Synthesis of Pyrethroids and Jasmonoids through Palladium-Catalyzed Cross-Coupling Reactions

Authors

Florencia Parpal

^aDepartamento de Química del Litoral, Centro Universitario Regional Litoral Norte, Universidad de la República, Ruta 3 km 363, Paysandú 60000, Uruguay
Ana Paula Paullier

^aDepartamento de Química del Litoral, Centro Universitario Regional Litoral Norte, Universidad de la República, Ruta 3 km 363, Paysandú 60000, Uruguay
Enrique Pandolfi

^bLaboratorio de Síntesis Orgánica, Departamento de Química Orgánica, Facultad de Química, Universidad de la República, General Flores 2124, Montevideo 11800, Uruguay
Viviana Heguaburu∗

^aDepartamento de Química del Litoral, Centro Universitario Regional Litoral Norte, Universidad de la República, Ruta 3 km 363, Paysandú 60000, Uruguay

Abstract

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Abstract

The synthesis of jasmone and related jasmonoids and pyrethroids is described. These compounds play a defensive role in plants and share a common cyclopentenone core with variations in the side chains. Jasmone, cinerone, allylrethrone, and derivatives were synthesized through π-allyl palladium cross-coupling of stannane derivatives. With selective hydrogenation, dihydrojasmone, and dihydrocinerone were also synthesized.

Key words

allylrethrone - cinerone - cross-coupling - dihydrojasmone - jasmone

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References

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Supplementary Material

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