Synthetic Studies on Newly Designed Biologically Active Compounds Related to Physiologically Important Substances

新设计的与重要生理物质相关的生物活性化合物的合成研究

• 批准号: 62470141
• 负责人: IKEGAMI Shiro
• 金额: $ 3.58万
• 依托单位: Teikyo University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for General Scientific Research (B)
• 财政年份: 1987
• 资助国家: 日本
• 起止时间: 1987 至 1988
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-62470141/
• 关键词: Prostaglandin; Prostacyclin; Prostacyclin carbon analogue; leukotriene; Leukotriene B_4; Lipoxin A; Lipoxin B; Bicyclo[3.3.0]octenone; Bicyclo[3.3.0]octenol; Carbenoid; ロイコトリエンB_4類縁体; カルベノイド; ビニルシクロプロパン; シクロペンテン転位

Our researches carried out in 1987-1988 are as follows.1) Based on our initial discovery of isocarbacyclin, a stable prostacyclin carbon analogue, we established its new synthetic routs.2) We accomplished the efficient synthetic method for the ideal synthetic intermediate, bicyclo[3.3.0]oct-6-en-2-one and the related derivatives in optically active forms by means of either optical resolution or asymmetric synthesis.3) We discovered the new synthetic methodology for the construction of the alfa and omega chains of prostablandins and achieved the synthesis of isocarbacyclin by its application.4) We wynthesized the newly designed furan-containing tricyclic prostacyclin analobue by employing a base-promoted cyclization for the construction of a tricyclic furan ring.5) We newly designed benzene-containing analogues related to leukotriene B_4 and achieved its first synthesis.6) We discovered novel and effective methods for alfa-thioalkylation of aromatic compounds, which was used for the synthesis of a benzene-containing analogue related to lipoxin A and B.7) Concerning the synthesis of biologically active glycosides, we established the efficient method for the stereoselective glycosylation by the use of phosphate esters.

1987-1988年，我们进行了以下研究：1）在首次发现稳定的前列环素碳类似物isocarbacyclin的基础上，建立了其新的合成路线; 2）完成了理想合成中间体的高效合成方法，二环[3.3.0]辛-6-烯-2-酮和相关衍生物的光学活性形式，通过光学拆分或不对称合成。我们发现了前列腺素α链和ω链的新合成方法，并应用该方法合成了异碳环素。4）我们通过碱促环化法合成了新设计的含呋喃的三环前列腺环素类似物。5）我们设计了苯-6）发现了一种新的有效的芳族化合物的α-硫代烷基化方法，并将其用于脂氧素A和B的含苯类似物的合成。7）在生物活性糖苷的合成方面，我们建立了利用磷酸酯进行立体选择性糖基化的有效方法。

项目成果

Y.Torisawa;K.Satoh;S.Ikegami: Heterocycles. (1989)

Y.Torisawa；K.Satoh；S.Ikegami：杂环。

S.Hashimoto;M.Sonegawa;S.Sakata;S.Ikegami: J.Chem.Soc.,Chem.Commun.637-640 (1987)

S.Hashimoto；M.Sonekawa；S.Sakata；S.Ikegami：J.Chem.Soc.，Chem.Commun.637-640 (1987)

Y.Torisawa; K.Satoh; S.Ikegami: "Synthesis of a Novel Furan-Containing Tricyclic Prostacyclin Analogue" Heterocycles. (1989)

Y.鸟泽;

S.Hashimoto,T.Shinoda,S.Ikegami: J.Chem.Soc.,Chem.Commun.1137-1139 (1989)

S.Hashimoto、T.Shinoda、S.Ikegami：J.Chem.Soc.、Chem.Commun.1137-1139 (1989)

S.Hashfmoto;T.Shinoda;and S.Ikegami: Tetrahedron Letters. 27. 2885-2888 (1986)

S.Hashfmoto；T.Shinoda；和 S.Ikegami：四面体字母。