Stereoisomers and analogs of 14-methyl-1-octadecene, sex pheromone of peach leafminer moth,Lyonetia clerkella, L.

Sonnet, Philip E.; Proveaux, A. T.; Adamek, E.; Sugie, Hajime; Sato, Rikio; Tamaki, Yoshio

doi:10.1007/bf01880098

Cited by 11 publications

(2 citation statements)

References 9 publications

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“…Sugie et al first isolated (S)−14-methyl-1-octadecene (1) (Figure 1) as the sex pheromone of the peach leafminer moth, 2 and the synthesis of the racemic form of 1 was then achieved by a couple of teams. [3][4][5] It was revealed that the Sisomer was active through lure experiments on peach leafminer moths, while the Risomer was almost inactive. 6 Recently, Ando disclosed an informal synthesis of (±)−1, employing Schlosser's copper-catalyzed Grignard reaction.…”

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confidence: 99%

A New Asymmetric Synthesis of (S)-14-Methyl-1-Octadecene, the Sex Pheromone of the Peach Leafminer Moth

Liu

Rao

et al. 2021

Natural Product Communications

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An asymmetric synthesis of 14-methyl-1-octadecene, the sex pheromone of the peach leafminer moth, has been efficiently achieved. A key chiral intermediate, ( R)−4-(benzyloxy)−3-methylbutanal, which has been developed as the resource chemical, can be obtained in large quantities from the steroid industry. 1,11-Undecanediol is selectively masked, and then converted into a phosphonium salt derivative, thereby effectively constructing a carbon skeleton. The target molecule is synthesized in 8 linear steps, with a 42% yield. The key characteristic of our synthesis lies in its chiral-pool strategy.

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confidence: 99%

A New Asymmetric Synthesis of (S)-14-Methyl-1-Octadecene, the Sex Pheromone of the Peach Leafminer Moth

Liu

Rao

et al. 2021

Natural Product Communications

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“…This paper now describes the generation of optically pure 2-methylbutanoic acid (1), 2-methylpentanoic acid (2) 2-methylhexanoic acid (3), 2-ethylhexanoic acid (4), the corresponding alcohols 2-methyl-butan-l-01 (5), 2-methyl-pentan-I-ol (6), 2-methyl-hexan-I-ol (7), 2-ethyl-hexan-l-ol (8) and the esters etlJyl-2-methylbutanoate (9) and prenyl-2-methylpentanoate (10).…”

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confidence: 99%

Chiral 2-alkylbranched acids, esters and alcohols. Preparation and stereospecific flavour evaluation

Rettinger

Burschka

Scheeben

et al. 1991

Tetrahedron: Asymmetry

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Racemic 2-alkylbranched acids are transformed to diastereomeric derivatives with (S)-2-hydroxy-3-phenylpropionic acid-N-methylamide or (S)-(-)-l-phenylethylamine and separated by liquid chromatography to pure diastereoisomers, which are subsequently hydrolyzed to yield optically pure acids. Enantiomeric alcohols are generated by LiAlH 4 -reduction of the corresponding acids, esters are synthesized by different methods. The odour impression of the enantiomeric compounds is investigated.2-Alkylalkanoic acids, esters and alcohols are well appreciated aroma compounds of fruits and other foodstuffs 1). In particuliar 2-methylbutanoic acid and its esters are known to be important compounds of fruits like apples 2) and pineapples 3). Until now odour quality only was investigated with racemic substances of this type, although it is generally known that enantiomers may exhibit rather different odour sensations 4 ). 2-Alkylbranched acids and alcohols are important for pheromone synthesis and liquid crystal investigations, too. Recently, investigations on lipase-catalyzed enantioselective esterification of 2-methylalkanoic acids have been reported by EngeI 5 ).This paper now describes the generation of optically pure 2-methylbutanoic acid (1), 2-methylpentanoic acid (2) 2-methylhexanoic acid (3), 2-ethylhexanoic acid (4), the corresponding alcohols 2-methyl-butan-l-01 (5), 2-methyl-pentan-I-ol (6), 2-methyl-hexan-I-ol (7), 2-ethyl-hexan-l-ol (8) and the esters etlJyl-2-methylbutanoate (9) and prenyl-2-methylpentanoate (10).In order to determine their absolute configurations racemic acids 1-4 were converted to diastereomeric amides with (S)-(-)-l-phenylethylamine (SPEA) and chromatographically (LC) separated into optically pure diastereoisomers. Diastereomeric amides were prepared either by a way earlier described by Kaneda 6 ) with equimolar ratio of free acid and free amide by catalysis of N,N'-Dicylclohexylcarbodiimide (DCC) in dry tetrahydrofurane (THF) or by an other way versus acid chloride and free amine under catalysis of 4-Dimethylaminopyridine (DMAP). Absolute configurations of the 2-alkylalkanoic acids moieties were eludicated by comparison with easily available (S)-2-methylbutanoic acid la and by IH-NMR data of tlJeir diastereomeric (S)-1-phenylethylamides 7 ) (Helmchen's model), by chromatographic behaviour of tlJese 965

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The Synthesis of Insect Pheromones, 1979–1989

Mori

1992

Total Synthesis of Natural Products

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Stereoisomers and analogs of 14-methyl-1-octadecene, sex pheromone of peach leafminer moth,Lyonetia clerkella, L.

Cited by 11 publications

References 9 publications

A New Asymmetric Synthesis of (S)-14-Methyl-1-Octadecene, the Sex Pheromone of the Peach Leafminer Moth

A New Asymmetric Synthesis of (S)-14-Methyl-1-Octadecene, the Sex Pheromone of the Peach Leafminer Moth

Chiral 2-alkylbranched acids, esters and alcohols. Preparation and stereospecific flavour evaluation

The Synthesis of Insect Pheromones, 1979–1989

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