Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2024 May 4;29(9):2136.
doi: 10.3390/molecules29092136.

Asymmetric Synthesis of Three Alkenyl Epoxides: Crafting the Sex Pheromones of the Elm Spanworm and the Painted Apple Moth

Yun Zhou  1 , Jianan Wang  2 , Beijing Tian  1 , Yanwei Zhu  1 , Yujuan Zhang  1 , Jinlong Han  1 , Jiangchun Zhong  2 , Chenggang Shan  1
Affiliations

Asymmetric Synthesis of Three Alkenyl Epoxides: Crafting the Sex Pheromones of the Elm Spanworm and the Painted Apple Moth

Yun Zhou et al. Molecules. .

Abstract

A concise synthesis of the sex pheromones of elm spanworm as well as painted apple moth has been achieved. The key steps were the alkylation of acetylide ion, Sharpless asymmetric epoxidation and Brown's P2-Ni reduction. This approach provided the sex pheromone of the elm spanworm (1) in 31% total yield and those of the painted apple moth (2, 3) in 26% and 32% total yields. The ee values of three final products were up to 99%. The synthesized pheromones hold promising potential for use in the management and control of these pests.

Keywords: alkenyl epoxides; asymmetric synthesis; elm spanworm; painted apple moth; sex pheromone.

PubMed Disclaimer

Conflict of interest statement

The authors declare no conflicts of interest.

Figures

Figure 1
Figure 1
The sex pheromones of the elm spanworm and the painted apple moth.
Scheme 1
Scheme 1
Retrosynthetic analysis of the sex pheromone 1.
Scheme 2
Scheme 2
Synthesis of chiral epoxy alcohols 14–16.
Scheme 3
Scheme 3
Synthesis of target compounds 1, 2 and 3.
See this image and copyright information in PMC

References

    1. Ando T., Inomata S., Yamamoto M. Lepidopteran sex pheromones. Top. Curr. Chem. 2004;239:51–96. - PubMed
    1. Ciesla W.M. Life History and Habits of the Elm Spanworm, Ennomos subsignarius, in the Southern Appalachian Mountains (Lepidoptera: Geometridae) Ann. Entomol. Soc. Am. 1964;57:591–596. doi: 10.1093/aesa/57.5.591. - DOI
    1. Ryall K., Silk P.J., Wu J.-P., Mayo P., Lemay M.A., MaGee D. Sex pheromone chemistry and field trapping studies of the elm spanworm Ennomos subsignaria (Huebner) (Lepidoptera:Geometridae) Naturwissenschaften. 2010;97:717–724. doi: 10.1007/s00114-010-0687-6. - DOI - PubMed
    1. MaGee D.I., Silk P.J., Wu J., Mayo P.D., Ryall K. Synthesis of chiral alkenyl epoxides: The sex pheromone of the elm spanworm Ennomos subsignarius (Hubner) (Lepidoptera: Geometridae) Tetrahedron. 2011;67:5329–5338. doi: 10.1016/j.tet.2011.05.015. - DOI
    1. Muto S.-e., Mori K. Synthesis of the four components of the female sex pheromone of the painted apple moth, Teia anartoides. Biosci. Biotechnol. Biochem. 2003;67:1559–1567. doi: 10.1271/bbb.67.1559. - DOI - PubMed

LinkOut - more resources