A New Synthesis of the Sex Pheromone of the Indian Meal Moth Plodia Interpunctella hb. (Lepidoptera, Pyralidae)

Andreica, Adriana-Maria; Gansca, Lucia; Ciotlaus, Irina; Oprean, Ioan

Adriana-Maria Andreica, Lucia Gansca, Irina Ciotlaus, Ioan Oprean

A New Synthesis of the Sex Pheromone of the Indian Meal Moth Plodia Interpunctella hb. (Lepidoptera, Pyralidae)

Abstract:

Abstract: New synthesis of (9Z,12E)-9,12-tetradecadien-1-yl acetate, the sex pheromone of the indian meal moth Plodia interpunctella (Lepidoptera, Pyralidae), were developed. The synthesis was based on a C8+C2=C10 and C10+C4=C12 coupling scheme. 1,8-Octanediol is the starting material used in the synthesis. The route involves, as the key step, the use of the mercury derivative of the terminal alkyne omega functionalised as intermediate. The first coupling reaction took place between 1-tert-butoxy-8-bromo-octane and lithium acetylide-ethylendiamine complex obtaining 1-tert-butoxy-dec-9-yne, which is transformed in di[tert-butoxy-dec-9-yne]mercury. In the second coupling reaction, the mercury derivative was directly lithiated and then alkylated with (E)-1-bromo-2-butene obtaining 1-tert-butoxy-(9-yne,12E)-9,12-tetradecaenyne. After stereoselective reduction in the presence of Ni-P2 catalyst and acetylation gave (9Z,12E)-9,12-tetradecadien-1-yl acetate with 82% isomeric purity. Keywords: (9Z,12E)-9,12-tetradecadien-1-yl acetate, Lepidoptera, sex pheromone, Plodia interpunctella

Keywords:
(9Z;12E)-9;12-tetradecadien-1-yl acetate; Lepidoptera; sex pheromone; Plodia interpunctella

Issue: 2020, Volume 71, Issue 1

Pages: 201-205

Publication date: 2020/2/7

https://doi.org/10.37358/RC.20.1.7832

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Citation Styles

Cite this article as:
ANDREICA, A., GANSCA, L., CIOTLAUS, I., OPREAN, I., A New Synthesis of the Sex Pheromone of the Indian Meal Moth Plodia Interpunctella hb. (Lepidoptera, Pyralidae), Rev. Chim., 71(1), 2020, 201-205.

Vancouver
Andreica A, Gansca L, Ciotlaus I, Oprean I. A New Synthesis of the Sex Pheromone of the Indian Meal Moth Plodia Interpunctella hb. (Lepidoptera, Pyralidae). Rev. Chim.[internet]. 2020 Jan;71(1):201-205. Available from: https://doi.org/10.37358/RC.20.1.7832

APA 6th edition
Andreica, A., Gansca, L., Ciotlaus, I. & Oprean, I. (2020). A New Synthesis of the Sex Pheromone of the Indian Meal Moth Plodia Interpunctella hb. (Lepidoptera, Pyralidae). Revista de Chimie, 71(1), 201-205. https://doi.org/10.37358/RC.20.1.7832

Harvard
Andreica, A., Gansca, L., Ciotlaus, I., Oprean, I. (2020). 'A New Synthesis of the Sex Pheromone of the Indian Meal Moth Plodia Interpunctella hb. (Lepidoptera, Pyralidae)', Revista de Chimie, 71(1), pp. 201-205. https://doi.org/10.37358/RC.20.1.7832

IEEE
A. Andreica, L. Gansca, I. Ciotlaus, I. Oprean, "A New Synthesis of the Sex Pheromone of the Indian Meal Moth Plodia Interpunctella hb. (Lepidoptera, Pyralidae)". Revista de Chimie, vol. 71, no. 1, pp. 201-205, 2020. [online]. https://doi.org/10.37358/RC.20.1.7832

Text
Adriana-Maria Andreica, Lucia Gansca, Irina Ciotlaus, Ioan Oprean,
A New Synthesis of the Sex Pheromone of the Indian Meal Moth Plodia Interpunctella hb. (Lepidoptera, Pyralidae),
Revista de Chimie,
Volume 71, Issue 1,
2020,
Pages 201-205,
ISSN 2668-8212,
https://doi.org/10.37358/RC.20.1.7832.
(https://revistadechimie.ro/Articles.asp?ID=7832)
Keywords: (9Z;12E)-9;12-tetradecadien-1-yl acetate; Lepidoptera; sex pheromone; Plodia interpunctella

RIS
TY - JOUR
T1 - A New Synthesis of the Sex Pheromone of the Indian Meal Moth Plodia Interpunctella hb. (Lepidoptera, Pyralidae)
A1 - Andreica, Adriana-Maria
A2 - Gansca, Lucia
A3 - Ciotlaus, Irina
A4 - Oprean, Ioan
JF - Revista de Chimie
JO - Rev. Chim.
PB - Revista de Chimie SRL
SN - 2668-8212
Y1 - 2020
VL - 71
IS - 1
SP - 201
EP - 205
UR - https://doi.org/10.37358/RC.20.1.7832
KW - (9Z
KW - 12E)-9
KW - 12-tetradecadien-1-yl acetate
KW - Lepidoptera
KW - sex pheromone
KW - Plodia interpunctella
ER -

BibTex
@article{RevCh2020P201,
author = {Andreica Adriana-Maria and Gansca Lucia and Ciotlaus Irina and Oprean Ioan},
title = {A New Synthesis of the Sex Pheromone of the Indian Meal Moth Plodia Interpunctella hb. (Lepidoptera, Pyralidae)},
journal = {Revista de Chimie},
volume = {71},
number = {1},
pages = {201-205},
year = {2020},
issn = {2668-8212},
doi = {https://doi.org/10.37358/RC.20.1.7832},
url = {https://revistadechimie.ro/Articles.asp?ID=7832}
}

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