1998 年度実績報告書

昆虫・藻類および哺乳類のフェロモンの化学合成

研究課題

研究課題/領域番号	09680576
研究機関	東京理科大学
研究代表者	森謙治東京理科大学, 理学部・第2部, 教授 (20011843)
研究分担者	滝川浩郷東京理科大学, 理学部・第2部, 助手 (40271332)
キーワード	フェロモン / 光学活性体 / 不斉合成
研究概要	1) 単細胞緑鞭毛藻であるChlamydomonas allensworthiiの雌性配偶子が放出する性フェロモンであるlurlenic acidとその類縁体を多数合成し、フェロモン活性の発現にはD-キシロース部分の他に、芳香環の水酸基部分と末端に極性基を有する不飽和側鎖が重要なことを明らかにした。 2) キクイムシの一種のフェロモンである(-)-frontalinの簡便な合成法を開発した。 3) ジンサンシバンムシ(Stegobium paniceum)のフェロモンであるstegobiolとstegobinoneとを高純度結晶として合成した。 4) 粘液細菌(Stigmatella aurantiaca)の子実体形成誘導フェロモンであるstigmolone(8-ヒトロキシ-2,5,8-トリメチル-4-ノナノン)の両鏡像体とラセミ体とを合成し、天然物はラセミ体であることを明らかにした。 5) Sandfly,(Lutzomyia longipalpis)の性フェロモンである3-methyl-α-himachaleneと9-methylgermacrene-Bのラセミ体を合成し、フェロモンの平面構造を確定させた。 6、イエネズミ(Mus musculus)の雄が生産する性フェロモンである2-sec-ブチル4,5-ジヒドロチアゾールの両鏡像体と(1R,5S,7R)-3,4-dehydro-exo-brevicominとを合成した。

研究成果
(14件)

すべてその他

すべて文献書誌 (14件)

[文献書誌] Kenji MORI: "Chirality and Insect Pheromones" Chirality. 10・7. 578-586 (1998)
[文献書誌] Kenji MORI: "Semiochemicals-Synthesis, Stereochemistry and Bioactivity" European Journal of Organic Chemistry. No.8. 1479-1489 (1998)
[文献書誌] S.Takanashi,K.Mori: "Synthesis of the Analogues of Lurlenic Acid with Modification in the Side-Chain or in the Aromatic Nucleus:Summary of the Structure-Activity Relationships" European Journal of Organic Chemistry. No.1. 43-55 (1998)
[文献書誌] Y.Nishimura,K.Mori: "A New Synthesis of (-)-Frontalin, the Bark Beetle Pheromone" European Journal of Organic Chemistry. 233-236 (1998)
[文献書誌] K.Mori,S.Sano,Y.Yokoyama,M.Bando,M.Kido: "Synthesis of Stegobiol and Its Oxidation to Stegobinone the Components of the Female-producead Sex Pheromone of the Dugstore" European Journal of Organic Chemistry. 1135-1148 (1998)
[文献書誌] K.Mori,M.Takenaka: "Synthesis of the Enantiomers of 8-Hydroxy-2.5,8-trimethyl-4-nonano the Myxobacterial Pheromone of Stigmatella aurantiaca" European Journal of Organic Chemistry. 2181-2184 (1998)
[文献書誌] K.Domon,K.Mori: "Simple Synthesis of (±)-Stigmolone (8-Hydroxy-2.5,8-Trimethyl-4-nonanone), the Pheromone of Stigmatella aurantiaca" European Journal of Organic Chemistry. 印刷中. (1999)
[文献書誌] J.G.C.Hamilton,A.M.Hooper,K.Mori,J.A.Pickett,S.Sano: "3-methyl-α-himachalene Confirmed and the relative stereochemisty defined by synthesis as the sex pheromone of the sandfly" Chemical Communications. 印刷中. (1999)
[文献書誌] 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)
[文献書誌] 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)
[文献書誌] T.Tashiro,K.Mori: "Synthesis of the Enantiomers of 2-sec-Butyl-4,5-dihydrothiazok and (1R,5S,7R)-3,4-Dehydro-exo-brevicomin, the Pheromone" European Journal of Organic Chemistry. 印刷中. (1999)
[文献書誌] Kenji MORI (J.G.Millar,K.F.Haynes編): "Methods in Chemical Ecology Volume 1. Chapter 8:Separation of Enantiomers and Determination of Absolute Configuration" Kluwer Academic Publishers, 390(295-338) (1998)
[文献書誌] Kenzi Mori (N.Kurihara, J.Miyamoto編): "Chirality in Agrochemicals Chapter 6:Chirality in Insect Juvenile Hormones and Pheromones" John Wiley & Sons, 269(199-257) (1998)
[文献書誌] Kenji MORI (Kenji MORI編): "Comprehensive Natural Products Chemistry Vol8. Chapter1:Overview" Elsevcer Science Ltd., 749(1-18) (1999)

1998 年度 実績報告書

昆虫・藻類および哺乳類のフェロモンの化学合成

研究代表者

森 謙治 東京理科大学, 理学部・第2部, 教授 (20011843)

研究成果

[文献書誌] Kenji MORI: "Chirality and Insect Pheromones" Chirality. 10・7. 578-586 (1998)

[文献書誌] Kenji MORI: "Semiochemicals-Synthesis, Stereochemistry and Bioactivity" European Journal of Organic Chemistry. No.8. 1479-1489 (1998)

[文献書誌] S.Takanashi,K.Mori: "Synthesis of the Analogues of Lurlenic Acid with Modification in the Side-Chain or in the Aromatic Nucleus:Summary of the Structure-Activity Relationships" European Journal of Organic Chemistry. No.1. 43-55 (1998)

[文献書誌] Y.Nishimura,K.Mori: "A New Synthesis of (-)-Frontalin, the Bark Beetle Pheromone" European Journal of Organic Chemistry. 233-236 (1998)

[文献書誌] K.Mori,S.Sano,Y.Yokoyama,M.Bando,M.Kido: "Synthesis of Stegobiol and Its Oxidation to Stegobinone the Components of the Female-producead Sex Pheromone of the Dugstore" European Journal of Organic Chemistry. 1135-1148 (1998)

[文献書誌] K.Mori,M.Takenaka: "Synthesis of the Enantiomers of 8-Hydroxy-2.5,8-trimethyl-4-nonano the Myxobacterial Pheromone of Stigmatella aurantiaca" European Journal of Organic Chemistry. 2181-2184 (1998)

[文献書誌] K.Domon,K.Mori: "Simple Synthesis of (±)-Stigmolone (8-Hydroxy-2.5,8-Trimethyl-4-nonanone), the Pheromone of Stigmatella aurantiaca" European Journal of Organic Chemistry. 印刷中. (1999)

[文献書誌] J.G.C.Hamilton,A.M.Hooper,K.Mori,J.A.Pickett,S.Sano: "3-methyl-α-himachalene Confirmed and the relative stereochemisty defined by synthesis as the sex pheromone of the sandfly" Chemical Communications. 印刷中. (1999)

[文献書誌] 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)

[文献書誌] 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)

[文献書誌] T.Tashiro,K.Mori: "Synthesis of the Enantiomers of 2-sec-Butyl-4,5-dihydrothiazok and (1R,5S,7R)-3,4-Dehydro-exo-brevicomin, the Pheromone" European Journal of Organic Chemistry. 印刷中. (1999)

[文献書誌] Kenji MORI (J.G.Millar,K.F.Haynes編): "Methods in Chemical Ecology Volume 1. Chapter 8:Separation of Enantiomers and Determination of Absolute Configuration" Kluwer Academic Publishers, 390(295-338) (1998)

[文献書誌] Kenzi Mori (N.Kurihara, J.Miyamoto編): "Chirality in Agrochemicals Chapter 6:Chirality in Insect Juvenile Hormones and Pheromones" John Wiley & Sons, 269(199-257) (1998)

[文献書誌] Kenji MORI (Kenji MORI編): "Comprehensive Natural Products Chemistry Vol8. Chapter1:Overview" Elsevcer Science Ltd., 749(1-18) (1999)

1998 年度実績報告書

森謙治東京理科大学, 理学部・第2部, 教授 (20011843)

[文献書誌] 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)