DIASTEREOSELECTIVE SYNTHESIS OF (8E,10Z)-TETRADECA-8,10-DIENAL, THE SEXUAL PHEROMONE OF THE HORSE-CHESTNUT LEAF-MINER Cameraria ohridella (LEPIDOPTERA: GRACILLARIIDAE)

Iuliana VASIAN; Teodora FLORIAN; Alexandrina NAN; Emese GAL; Monica GORGAN; Ștefania Maria TÖTÖS; Vasile FLORIAN; Ion OLTEAN

doi:10.24193/subbchem.2021.4.15

DIASTEREOSELECTIVE SYNTHESIS OF (8E,10Z)-TETRADECA-8,10-DIENAL, THE SEXUAL PHEROMONE OF THE HORSE-CHESTNUT LEAF-MINER Cameraria ohridella (LEPIDOPTERA: GRACILLARIIDAE)

Authors

Iuliana VASIAN Babeș-Bolyai University, Raluca Ripan Institute for Research in Chemistry, Pheromones Production Centre, Fântânele 30, 400084, Cluj-Napoca, Romania. *Corresponding author: iuliana.vasian@ubbcluj.ro, iulianavasian@yahoo.com. https://orcid.org/0000-0001-8520-2194
Teodora FLORIAN University of Agricultural Sciences and Veterinary Medicine Cluj-Napoca, Faculty of Agriculture, Department of Entomology, 3-5 Mănăştur Street, 400372, Cluj-Napoca, Romania.
Alexandrina NAN National Institute for Research and Development of Isotopic and Molecular Technologies, 67-103 Donat Str., 400293 Cluj-Napoca, Romania. https://orcid.org/0000-0001-6898-2723
Emese GAL Babeş-Bolyai University, Faculty of Chemistry and Chemical Engineering, 11 Arany Janos str., RO-400028, Cluj-Napoca, Romania. https://orcid.org/0000-0003-4324-0787
Monica GORGAN Babeș-Bolyai University, Raluca Ripan Institute for Research in Chemistry, Pheromones Production Centre, Fântânele 30, 400084, Cluj-Napoca, Romania.
Ștefania Maria TÖTÖS Babeș-Bolyai University, Raluca Ripan Institute for Research in Chemistry, Pheromones Production Centre, Fântânele 30, 400084, Cluj-Napoca, Romania. https://orcid.org/0000-0003-4279-6142
Vasile FLORIAN University of Agricultural Sciences and Veterinary Medicine Cluj-Napoca, Faculty of Agriculture, Department of Entomology, 3-5 Mănăştur Street, 400372, Cluj-Napoca, Romania. https://orcid.org/0000-0002-5093-1722
Ion OLTEAN University of Agricultural Sciences and Veterinary Medicine Cluj-Napoca, Faculty of Agriculture, Department of Entomology, 3-5 Mănăştur Street, 400372, Cluj-Napoca, Romania.

DOI:

https://doi.org/10.24193/subbchem.2021.4.15

Keywords:

Cameraria ohridella, (8E,10Z)-tetradeca-8,10-dienal, Pheromone, Lure, Field Tests.

Abstract

Versatile classical and modern methods for a new synthesis of (8E,10Z)-tetradeca-8,10-dienal based on Sonogashira cross-coupling, Cahiez-Fürstner reaction as well as other reactions using palladium, iron or copper as catalysts were described. We designed two ways employing two different strategies one of that involves an E-reduction and the other a Z-reduction with crucial importance in terms of diastereoselective synthesis. From the variously formulated pheromone baits, the one containing only the active isomer showed superior activity compared to the mixture of all isomers of 8,10-tetradecandienal. The synthesis of the pure E,Z diastereoisomer allowed to clarify their structure-bioactivity relationships to reveal the diversity in the stereochemical aspects of pheromone communications.

References

G. Deschk; N. Dimic; Acta Entomol. Jugosl., 1986, 22, 11–23.

T. Perju; I. Oltean; I. Oprean; M. Ecobici; J. Centr. Eur. Agric., 2004, 4, 331-336.

D. I. Șandru; Sănătatea plantelor, 1998, 6, 29-34.

a. A. Svatoš; B. Kalinová; H. Michal; J. Kindl; O. Hovorka; H. Ivan; Tetrahedron Lett., 1999b, 40, 7011-7014. b. A. Svatoš; B. Kalinová; H. Michal; J. Kindl; O. Hovorka; H. Ivan; IOBC wprs Bulletin, 2001, 24, 5-12.

B. Kalinová; A. Svatoŝ; J. Kindl; O. Hovorka; I. Hrdý; J. Kuldová; M. Hoskovec; J. Chem. Ecol., 2003, 29, 387-404.

M. Hoskovec; A. Šaman; A. Svatoš; Collect. Czech. Chem. Commun., 2000, 65, 511-523.

W. Francke; S. Franke; J. Bergmann; T. Tolasch; M. Subchev; A. Mircheva; T. Toshova; A. Svatos; B. Kalinova; Z. Karpati; G. Szocs; M. Toth; Naturforsch. C: Biosci., 2002, 57, 739-752.

R. Marcia de Figueiredo; R. Berner; J. Julis; T. Liu; D. Türp; M. Christmann; J. Org. Chem., 2007, 72, 640-642.

L. Gânscă; S. Maxim; I. Ciotlăuș; A. Andreica; I. Oprean; Rev. Roum. Chim., 2011, 56, 895-899.

P. Chourreu; O. Guerret; L. Guillonneau; E. Gayon; G. Lefèvre; Org. Process Res. Dev., 2020, 24, 1335−1340.

J. Grodner; Tetrahedron, 2009, 65, 1648-1654.

K. Sonogashira; Y. Tohda; N. Hagihara; Tetrahedron Lett., 1975, 16, 4467-4470.

a. R. Rossi; A. Carpita; Synthesis, 1977, 8, 561-562. b. A. Parenty; J. -M. Campagne; Tetrahedron Lett., 2002, 43, 1231-1233.

T. Turki; S. Khamri; H. Amri; J. Soc. Chim. Tunis., 2007, 9, 17-22.

W. N. Smith; O. F. Beumel Jr.; Synthesis, 1974, 1, 441-442.

G. Cahiez; H. Avedissian; Synthesis, 1998, 8, 1199-1205.

A. Fürstner; A. Leitner; M. Méndez; H. Krause; J. Am. Chem. Soc., 2002, 124, 13856-13863.

J. H. V. Boom; J. D. M Herschied; C.B. Reese; Synthesis, 1973, 167-169.

E.J. Corey; J.W. Suggs; Tetrahedron Lett., 1975, 16, 2647-2650.

I. Vasian; I. Oprean; T. Florian; I. Oltean; Ecomoni utilizati in protectia plantelor, Editura Bioflux, 2018, ISBN 978-606-8887-28-9, chapter 1.

C. A. Brown; J. Org. Chem., 1970, 35, 1900-1904.

H. C. Brown; Organic Syntheses via Boranes; Wiley-Interscience: New York, 1975.

A. Singh; M. L. Sharma; J. Singh; Indian Journal of Chemistry, 2010, 49B, 1648-1652.

O. Loreau; A. Maret; J. M. Chardigny; J. L. Sébédio; J. P. Noël; Chemistry and Physics of Lipids, 2001, 110, 57-67.

STUDIA UBB CHEMIA, Volume 66 (LXVI), No. 4, December 2021

Downloads

Published

2021-12-30

How to Cite

VASIAN, I., FLORIAN, T., NAN, A., GAL, E., GORGAN, M., TÖTÖS, Ștefania M., … OLTEAN, I. (2021). DIASTEREOSELECTIVE SYNTHESIS OF (8E,10Z)-TETRADECA-8,10-DIENAL, THE SEXUAL PHEROMONE OF THE HORSE-CHESTNUT LEAF-MINER Cameraria ohridella (LEPIDOPTERA: GRACILLARIIDAE). Studia Universitatis Babeș-Bolyai Chemia, 66(4), 205–224. https://doi.org/10.24193/subbchem.2021.4.15