Total synthesis of (6R,12R)-6,12-dimethylpentadecan-2-one, the sex pheromone of Diabrotica balteata LeConte

Chirality. 2024 Mar;36(3):e23658. doi: 10.1002/chir.23658.

Abstract

Diabrotica balteata LeConte is one of the most important polyphagous agricultural pests. The sex pheromone of this pest was synthesized using Evans asymmetric alkylation, ring-opening reaction of (R)-2-methyloxirane, SN 2 alkylation of secondary tosylate, and coupling of chiral tosylate with Grignard reagent as central strategies. The sex pheromone prepared herein would be useful to control D. balteata.

Keywords: (6R,12R)-6,12-dimethylpentadecan-2-one; banded cucumber beetle; chiral auxiliary; sex pheromone; total synthesis.

MeSH terms

  • Alkylation
  • Animals
  • Coleoptera*
  • Sex Attractants*
  • Stereoisomerism

Substances

  • 6,12-dimethylpentadecan-2-one
  • Sex Attractants