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Syntheses of optically active insect pheromones, (2R,5S)-2-methyl-5-hexanolide, (3S,11S)-3,11-dimethyl-2-nonacosanone, and serricornin

✍ Scribed by Tsutomu Katsuki; Masaru Yamaguchi

Book ID: 104227438
Publisher: Elsevier Science
Year: 1987
Tongue: French
Weight: 212 KB
Volume: 28
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)95804-0

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✦ Synopsis

Three insect pheromones, (2!,5S)-P-methyl-5-hexanolide, (3z,llSl-3,11-dimethyl-2-nonacosanone, and serricornin, were synthesized in optically pure forms by using newly developed asymmetric reactions as key steps. Optically active insect pheromones have been one of the challenging targets of organic synthesis because of il the structural diversity for their often rather small molecules and ii) unique relationships between their stereochemistry and pheromone activity. 11 The latter especially demands the highly diastero-and enantioselective methods for their efficient synthesis. Recently, we found that the amide enolate (31 bearing optically active 2,5-bis(methoxymethoxymethyllpyrrolidine (1) as a chiral auxiliary reacted with various electrophiles with excellent diastereo and/or diastereoface selectivity of >95% de (Scheme 11.21

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