# Enantioselective Synthesis of the Sex Pheromone of Sitodiplosis mosellana (Géhin) and Its Stereoisomers

**Authors:** Jianan Wang, Xiaoyang Li, Yun Zhou, Qinghua Bian, Jiangchun Zhong

PMC · DOI: 10.3390/molecules30030671 · 2025-02-03

## TL;DR

This study describes the enantioselective synthesis of the sex pheromone of Sitodiplosis mosellana and its stereoisomers using a six-step chemical process.

## Contribution

The paper introduces a novel synthetic strategy for the sex pheromone and its stereoisomers using chiral epoxide ring opening and triple bond hydrogenation.

## Key findings

- The sex pheromone (2S,7S)-2,7-Nonanediyl dibutyrate and its three stereoisomers were successfully synthesized.
- The synthesis involved a six-step process with total yields of 59–64%.
- The method utilized chiral epoxide ring opening and hydrogenation of the triple bond as key steps.

## Abstract

(2S,7S)-2,7-Nonanediyl dibutyrate is the sex pheromone of Sitodiplosis mosellana (Géhin). In this study, this sex pheromone and its three stereoisomers were prepared. Central to this strategy was the ring opening of chiral epoxide with an alkynyllithium and the hydrogenation of the triple bond. Moreover, this approach consisted of six steps, and the total yields were 59–64%.

## Linked entities

- **Chemicals:** (2S,7S)-2,7-Nonanediyl dibutyrate (PubChem CID 12009994)
- **Species:** Sitodiplosis mosellana (taxon 263140)

## Full-text entities

- **Species:** Sitodiplosis mosellana (orange wheat blossom midge, species) [taxon 263140]

## Figures

5 figures with captions in the complete paper: https://tomesphere.com/paper/PMC11820043/full.md

---
Source: https://tomesphere.com/paper/PMC11820043