Pheromone synthesis. Part 243: Synthesis and biological evaluation of (3R,13R,1′S)-1′-ethyl-2′-methylpropyl 3,13-dimethylpentadecanoate, the major component of the sex pheromone of Paulownia bagworm, Clania variegata, and its stereois

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• 作者：Kenji Mori ; Takuya Tashiro ; Boguang Zhao ; David M. Suckling ; Ashraf M. El-Sayed
• 关键词：Clania variegata ; 3 ; 13-Dimethylpentadecanoic acid ; 2-Methyl-3-pentanol ; Olefin cross metathesis ; Pheromone
• 刊名：Tetrahedron
• 出版年：2010
• 出版时间：3 April 2010
• 年：2010
• 卷：66
• 期：14
• 页码：2642-2653
• 全文大小：512 K

文摘

All of the four stereoisomers of (1′S)-1′-ethyl-2′-methylpropyl 3,13-dimethylpentadecanoate, the major component of the female sex pheromone of Clania variegata, were synthesized by employing olefin cross metathesis as the key reaction and starting from (R)- or (S)-2-methyl-1-butanol, (R)- or (S)-citronellal, and (S)-2-methyl-3-pentanol. Their bioassay revealed the (3R,13R,1′S)-isomer as the bioactive one, whose more efficient synthesis was achieved in two different ways by employing Wittig reaction as the key step.