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  • Synthesis of all the stereoisomers of 6-methyl-2-octadecanone, 14-methyl-2-octadecanone, and 6,14-dimethyl-2-octadecanone, sex pheromone components of the Lyclene dharma dharma moth, from the enantiomers of citronellal.

Synthesis of all the stereoisomers of 6-methyl-2-octadecanone, 14-methyl-2-octadecanone, and 6,14-dimethyl-2-octadecanone, sex pheromone components of the Lyclene dharma dharma moth, from the enantiomers of citronellal.

Bioscience, biotechnology, and biochemistry (2012-10-11)
Yasumasa Shikichi, Kenji Mori
ABSTRACT

The enantiomers of citronellal were converted to all the stereoisomers of 6-methyl-2-octadecanone, 14-methyl-2-octadecanone, and 6,14-dimethyl-2-octadecanone, the female-produced sex pheromone components of the Lyclene dharma dharma moth. Three well-established procedures, the Wittig reaction, alkylation of alkynes, and acetoacetic ester synthesis, were employed for the carbon-carbon bond formation to connect the building blocks.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
(R)-(+)-Citronellal, technical grade
Supelco
(±)-Citronellal, analytical standard
Sigma-Aldrich
(S)-(−)-Citronellal, 96%
Sigma-Aldrich
(±)-Citronellal, natural, ≥85%, FCC, FG
Sigma-Aldrich
(±)-Citronellal, ≥95.0% (GC)