Biological and organic chemistry of methyl-branched insect pheromones basen on enantioselective syntheses
| Project/Area Number |
24580158
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Multi-year Fund |
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| Section | 一般 |
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| Research Field |
Bioproduction chemistry/Bioorganic chemistry
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| Research Institution | Tokyo University of Agriculture and Technology |
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Principal Investigator |
ANDO Tetsu 東京農工大学, (連合)農学研究科(研究院), 教授 (50151204)
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| Project Period (FY) |
2012-04-01 – 2015-03-31
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| Project Status |
Completed (Fiscal Year 2014)
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| 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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| Keywords | 昆虫フェロモン / キラル合成 / 立体化学 / 立体反転 / メチル分岐 / 鱗翅目昆虫 / 性誘引物質 / 天然物化学 / 立体選択的 / フェロモン受容機構 / セミオケミカル / キラルＨＰＬＣ / ハモグリガ |
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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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Report
(4 results)
Research Products
(14 results)
