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. 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.

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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.
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