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

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

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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

References

1a Roth K, Vaupel E. Chem. Unserer Zeit 2017; 51: 162
1b Staudinger H, Ružička L. Helv. Chim. Acta 1924; 7: 177

2 Carson R. Silent Spring . Fawcett Crest; New York: 1964
3 Crombie L, Elliott M. Prog. Chem. Org. Nat. Prod. 1961; 19: 120
4 Crombie L, Edgar AJ. B, Harper SH, Lowe MW, Thompson D. J. Chem. Soc. 1950; 3552
5 Pickett JA, Birkett MA, Bruce TJ, Chamberlain RG, Matthes MC, Napier JA, Smart LE, Woodcock CM. Phytochemistry 2007; 68: 22

6a Ružička L, Pfeiffer M. Helv. Chim. Acta 1933; 16: 1208
6b Birkett MA, Campbell CA. M, Chamberlain K, Guerrieri E, Hick AJ, Martin JL, Matthes M, Naiper JA, Pettersson J, Pickett JA, Poppy GM, Pow EM, Pye BJ, Smart LE, Wadhams GH, Wadhams LJ, Woodcock CM. Proc. Natl. Acad. Sci. U.S.A. 2000; 97: 9329

7 Dąbrowska P, Boland W. ChemBioChem 2007; 8: 2281
8 Kato T, Kimura H, Masuko T, Shimosuka Y. Chem. Pharm. Bull. 1980; 28: 349
9 Takahashi T, Hori K, Tsuji J. Chem. Lett. 1981; 1189
10 Kataoka H, Yamada T, Goto K, Tsuji J. US Patent 4575570A, 1986
11 Trost BM, Pinkerton AB. J. Org. Chem. 2001; 66: 7714
12 Oshima K, Yamamoto H, Nozaki H. J. Am. Chem. Soc. 1973; 95: 4446
13 Parpal F, Pandolfi E, Heguaburu V. Tetrahedron Lett. 2017; 58: 1965
14 Del Valle L, Stille JK, Hegedus LS. J. Org. Chem. 1990; 55: 3019

15a Djuardi E, Bovonsombar P, McNelis E. Synth. Commun. 1997; 27: 2497
15b Shipe WD, Sorensen EJ. Org. Lett. 2002; 4: 2063

16 Lamandè-Langle S, Abarbri M, Thibonnet J, Duchene A. J. Organomet. Chem. 2009; 694: 2368
17 Asaba T, Katoh Y, Urabe D, Inoue M. Angew. Chem. Int. Ed. 2015; 54: 14457
18 Kessler H, Oschkinat H, Griesinger C, Bermel W. J. Magn. Reson. 1986; 70: 106
19 Liu W, Lu GH. Grasas Aceites 2018; 69: 268
20 Ravasio N, Antenori M, Gargano M, Rossi M. J. Mol. Catal. 1992; 74: 267

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