18 Sandflyの性フェロモンとして単離されたホモセスキテルペン類の合成(口頭発表の部)
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The sandfly Lutzomyia longipalpis is the only vector of the protozoan parasite Leishmania chagasi, the causative agent of visceral leishmaniasis in South and Central America. In 1994 Hamilton et al. isolated the sex pheromone of male Lutzomyia longipalpis from Brazil, and confirmed its activity by bioassay. Subsequently in 1996, 9-methylgermacrene-B (1) and 3-methyl-α-himachalene (2) were proposed as the structures of the pheromone components on the basis of their MS and ^1H NMR studies. We synthesized all of their stereoisomers, and established the relative and absolute configuration of the natural pheromone components on the basis of their NMR and GC analysis. 9-Methylgermacrene-B [(±)-1] was synthesized by employing a cyclization reaction [(±)-12→(±)-13] as the key step. The product (±)-1 was shown to be the racemate of the male-produced sex pheromone of the sandfly Lutzomyia longipalpis from Lapinha, Brazil. Both the enantiomers of 9-methylgermacrene-B (1) were synthesized by starting from the enantiomers of methyl 3-hydroxy-2-methylpropanoate (2). The male-produced sex pheromone of the sandfly Lutzomyia longipalpis from Lapinha, Brazil, was identified as (S)-1 by GC comparison. Four stereoisomers (2a-d) of (±)-3-methyl-a-himachalene were synthesized by employing the intramolecular Diels-Alder reaction [(±)-45 to (±)-46] as the key-step. The male-produced sex pheromone of the sandfly Lutzomyia longipalpis from Jacobina, Brazil, was shown to possess the structure and possible absolute configuration as depicted in 2c.
- 天然有機化合物討論会の論文
- 1999-09-01
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- 18 Sandflyの性フェロモンとして単離されたホモセスキテルペン類の合成(口頭発表の部)