Total Synthesis of (2 R ,6 R ,10 R )‐6,10,14‐Trimethylpentadecan‐2‐ol, Major Component of the Courtship Pheromone of Aphomia sociella

ABSTRACT Aphomia sociella is a common parasite of bumblebee colonies. The major component of its courtship pheromone, (2 R ,6 R ,10 R )‐6,10,14‐trimethylpentadecan‐2‐ol, was prepared from two chiral sources of ( R )‐citronellol and ( R )‐propylene oxide. The chiral methyl at C6 was introduced through Evans’ chiral auxiliaries, and two chiral blocks were assembled by Wittig coupling. The target pheromone was obtained in 10‐step longest sequence and 26% overall yield. The synthetic pheromone would be used for the future management of the bumblebee wax moth.

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Journal
ChemistrySelect
Published
2026-09-29
DOI
https://doi.org/10.1002/slct.74614
Primary Topic
Bioactive Natural Diterpenoids Research
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article
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Total Synthesis of (2 R ,6 R ,10 R )‐6,10,14‐Trimethylpentadecan‐2‐ol, Major Component of the Courtship Pheromone of Aphomia sociella

Haixiang Gao, Qinghua Bian, Jiangchun Zhong, Jianan Wang et al.
ChemistrySelect
Bioactive Natural Diterpenoids Research
article

Total Synthesis of (2 R ,6 R ,10 R )‐6,10,14‐Trimethylpentadecan‐2‐ol, Major Component of the Courtship Pheromone of Aphomia sociella

Haixiang Gao, Qinghua Bian, Jiangchun Zhong, Jianan Wang, Xiaoyang Li, Yun Zhou
article en

Abstract

ABSTRACT Aphomia sociella is a common parasite of bumblebee colonies. The major component of its courtship pheromone, (2 R ,6 R ,10 R )‐6,10,14‐trimethylpentadecan‐2‐ol, was prepared from two chiral sources of ( R )‐citronellol and ( R )‐propylene oxide. The chiral methyl at C6 was introduced through Evans’ chiral auxiliaries, and two chiral blocks were assembled by Wittig coupling. The target pheromone was obtained in 10‐step longest sequence and 26% overall yield. The synthetic pheromone would be used for the future management of the bumblebee wax moth.

ChemistrySelectVol. 11(37)
Shandong Academy of Agricultural Sciences (CN), China Agricultural University (CN)
Life in Land
Openalex Percentile: Top 20%
Bioactive Natural Diterpenoids Research
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