| Budget Amount *help |
¥5,460,000 (Direct Cost: ¥4,200,000、Indirect Cost: ¥1,260,000)
Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2013: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2012: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
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| Outline of Final Research Achievements |
Methyl-branched insect pheromones are interesting natural products, which need studies on branched positions and the stereochemistry. We examined convenient and versatile synthetic methods to introduce branches at target positions stereoselectively, and established routes to prepare chiral synthetic units by an SN2 reaction of secondary tosylates derived from chiral propyleneoxide. By utilizing the units, the following sex pheromones were stereoselectively synthesized; 5,9-dimethylheptadecane and 10,14-dimethyloctadec-1-ene of leafminer moths, 3,13-dimethylpentadecanoate of a bag moth, 5-methylheptadecan-7-ol of a lichen moth, and 6,10,13-trimethyltetradecan-2-one of a stink bug.
In addition to the synthetic experiments, more than one hundred known methyl-branched pheromones were listed according to chemical groups, and their studies on identification, stereoselective synthesis, and biosynthesis were reviewed.
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