# A Concise Asymmetric Synthesis of the Aggregation Pheromone of Cryptolestes ferrugineus, Ferrulactone II, and Its Enantiomer

## TL;DR

Scientists developed an efficient way to synthesize a pheromone and its mirror image to study their biological effects.

## Contribution

A concise asymmetric synthesis of Ferrulactone II and its enantiomer using a series of efficient and stereoselective reactions.

## Key findings

- The synthetic route includes CBS reduction, zipper reaction, and copper(I)-catalyzed coupling.
- Structures and configurations were confirmed using NMR, HRMS, specific rotation, and ECD spectroscopy.
- The method enables reliable production of pheromone material for biological studies.

## Abstract

A concise and efficient synthesis of the aggregation pheromone of Cryptolestes ferrugineus, Ferrulactone II, and its enantiomer has been developed. The synthetic route features CBS reduction, the zipper reaction, a copper(I)-catalyzed coupling, stereoselective partial hydrogenation, Yamaguchi esterification, and the Mitsunobu inversion reaction. The structures and absolute configurations of both enantiomers of the target pheromone were confirmed by NMR, HRMS, specific rotation, and ECD spectroscopy. This study provides a reliable supply of material for further biological evaluation.