Chemical Synthesis of Pheromones of Insects, Flagellates and Mammals.

昆虫、鞭毛虫和哺乳动物信息素的化学合成。

• 批准号: 09680576
• 负责人: MORI Kenji
• 金额: $ 2.05万
• 依托单位: Science University of Tokyo
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (C)
• 财政年份: 1997
• 资助国家: 日本
• 起止时间: 1997 至 1998
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-09680576/
• 关键词: pheromones; optically active compounds; cymmetric synthesis

1. Lurlenic acid, the female-produced pheromone of the green flagellate Chlamydomonas allensworthii, and its analogues were synthesized. Structural requirements for the expression of the pheromone activity are the sugar-part, the phenol part and the unsaturated side-chain with a polar group at its end.2. Bark beetle pheromones such as endo-isobrevicomin, exo-isobrevicomin, bicolorin, frontalin etc. were synthesized.3. Stegobiol and stegobinone, the drugstore beetle pheromone, were synthesized.4. Stigmolone, the pheromone to induce the fruiting body formation of a myxobacterium Stigmatella aurantiaca, was synthesized. The natural pheromone is a racemate.5. The racemate of the male-produced sex pheromone of the sandfly Lutzomyia longipalpis, (*)-3-methyl-alpha-himachalene and (*)-9-methylgermacrene-B, were synthesized to establish the gross structures of the pheromone components.6. The enantiomers of 2-sec-butyl-4, 5-dihydrothiazole and (lR, 5S, 7R)-3, 4-dehydro-exo-brevicomin, the pheromone components of the house mouse Mus musculus, were synthesized.

1.合成了绿色鞭毛虫Chlamydiumallensworthii雌性信息素Lurlenic酸及其类似物。表达信息素活性的结构要求是糖部分、酚部分和末端带有极性基团的不饱和侧链.合成了小蠹信息素如内异小蠹信息素、外异小蠹信息素、bicolorin、frontalin等.合成了金龟子信息素Stegobiol和Stegobinone.合成了一种诱导黄色粘细菌Stigmatella aurantiaca子实体形成的信息素Stigmolone。天然信息素是外消旋体。合成了长须沙蝇雄性信息素的外消旋体（*）-3-甲基-α-喜玛拉雅烯和（*）-9-甲基大牛儿烯-B，建立了其信息素组分的结构.合成了小家鼠信息素成分2-仲丁基-4，5-二氢噻唑和（1 R，5S，7 R）-3，4-脱氢-exo-brevicomin的对映体。

项目成果

S.Takanashi, K.Mori: "Synthesis of the Analogues of Lurlent Acid with modification in the Side-chain or in the Aromatic Nucleus : Summary of the Structure-Activity Relationships" Eurupeam Journal of Organic Chemistry. 43-55 (1998)

S.Takanashi、K.Mori：“侧链或芳香核修饰的 Lurlent 酸类似物的合成：结构-活性关系总结”Europeam 有机化学杂志。

S.Muto,Y.Nishimura,K.Mori: "Synthesis of Germacrene-B and Its Extension to the Synthesis of (±)-9-Methylgermacrene-B, the Racemate of the Male-produced Sex Pheromone of the Sandfly" European Journal of Organic Chemistry. 印刷中. (1999)

S.Muto、Y.Nishimura、K.Mori：“Germacrene-B 的合成及其对 (±)-9-Mmethylgermacrene-B（白蛉雄性产生的性信息素的外消旋体）合成的延伸”欧洲期刊有机化学出版（1999）。

S.Takanashi, K.Mori: "Synthesis of the Analogues of Lurlemic Acid with a modified Sugar pant : Chlamydomonas responds only to the D-xyluside" Liebigs Annalen. 1081-1084 (1997)

S.Takanashi、K.Mori：“用改良糖裤合成 Lurlemic Acid 类似物：衣藻仅对 D-木糖苷有反应”Liebigs Annalen。

S.Sano, K.Mori: "Synthesis of (1R^*, 3R^*, 7R^*)-3-Methyl-α-himachalene, the Racemate of the Male-produced Sex Pheromone of the Sandfly" European Journal of Organic Chemistry. (印刷中). (1999)

S.Sano, K.Mori：“白蛉雄性产生的性信息素的外消旋体 (1R^*, 3R^*, 7R^*)-3-甲基-α-himachalene 的合成”《欧洲有机杂志》化学（正在出版）（1999）。

Y.Yokoyama, K.Mori: "Synthesis of (1R,1′R,5′R,7′R)-and (1S,1′R,5′R,7′R) -Hydroxy-exo- brevicomin" Liebigs Annalen. 845-849 (1997)

Y.Yokoyama，K.Mori：“(1R,1′R,5′R,7′R)-和(1S,1′R,5′R,7′R)-羟基-外短短蛋白的合成”李比格斯年鉴。845-849（1997）