Synthesis of the (5S,9R)-isomer of 5,9-dimethylpentadecane, the major component of the female sex pheromone of the coffee leaf miner moth, Leucoptera coffeella

(5S,9R)-5,9-Dimethylpentadecane, one of the stereoisomers of the major component of the female sex pheromone of the coffee leaf miner moth (Leucoptera coffeella), was synthesized by starting from (R)-3-methyl-4-butanolide and (S)-citronellal.

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(R)-2-Methyl-l-octanolC9H20O[α]D24=+12.1 (c 2.43, EtOH)Source of chirality: (R)-3-methyl-4-butanolideAbsolute configuration: (R)

(R)-2-Methyloctyl iodideC9H19I[α]D21=-2.3 (c 4.75, hexane)Source of chirality: (R)-3-methyl-4-butanolideAbsolute configuration: (R)

(6S,10R)-2,6,10-Trimethyl-2-hexadeceneC19H38[α]D16=+1.85 (c 3.23, hexane)Source of chirality: (R)-3-methyl-4-butanolide and (S)-citronellalAbsolute configuration: (6S,10R)

(4R,8R)-4,8-DimethyltetradecanalC16H32O[α]D22=+1.3 (c 3.41, hexane)Source of chirality: (R)-3-methyl-4-butanolide and (S)-citronellalAbsolute configuration: (4R,8R)

(5R,9R)-5,9-Dimethyl-1-pentadeceneC17H34[α]D21=+2.3 (c 2.89, hexane)Source of chirality: (R)-3-methyl-4-butanolide and (S)-citronellalAbsolute configuration: (5R,9R)

(5S,9R)-5,9-DimethylpentadecaneC17H36[α]D23=+1.0 (c 2.23, hexane)Source of chirality: (R)-3-methyl-4-butanolide and (S)-citronellalAbsolute configuration: (5S,9R)