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

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

Florencia Parpal
a   Departamento de Química del Litoral, Centro Universitario Regional Litoral Norte, Universidad de la República, Ruta 3 km 363, Paysandú 60000, Uruguay
,
Ana Paula Paullier
a   Departamento de Química del Litoral, Centro Universitario Regional Litoral Norte, Universidad de la República, Ruta 3 km 363, Paysandú 60000, Uruguay
,
Enrique Pandolfi
b   Laboratorio de Síntesis Orgánica, Departamento de Química Orgánica, Facultad de Química, Universidad de la República, General Flores 2124, Montevideo 11800, Uruguay
,
Viviana Heguaburu
a   Departamento de Química del Litoral, Centro Universitario Regional Litoral Norte, Universidad de la República, Ruta 3 km 363, Paysandú 60000, Uruguay
› Institutsangaben
Programa de Desarrollo de Ciencias Básicas (Grant No. PEDECIBA-PNUD/URU/06/004), Agencia Nacional de Investigación e Innovación (ANII; Grant Nos. POS_NAC_2012_1_8985 and POS_NAC_2014_1_10237'), and Comisión Sectorial de Investigación Científica.


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.

Supporting Information



Publikationsverlauf

Eingereicht: 02. November 2021

Angenommen nach Revision: 11. Januar 2022

Accepted Manuscript online:
11. Januar 2022

Artikel online veröffentlicht:
03. März 2022

© 2022. Thieme. All rights reserved

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