Study on the environmentally-suitable synthesis of plant conservation materials and medicines

植物保护材料和药物的环保合成研究

• 批准号: 07555282
• 负责人: TSUBOI Sadao
• 金额: $ 0.64万
• 依托单位: Okayama University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (A)
• 财政年份: 1995
• 资助国家: 日本
• 起止时间: 1995 至 1996
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-07555282/
• 关键词: plant conservation material; bakers' yeast; lipase; optically active compound; biological catalyst; medicine; antitumor compound; highly selective reaction; 昆虫フェロモン; (-)-ディスパーラー; ペスタロチン; 高立体選択的合成

In this project, we suceeded in the syntheses of chiral alcohols, epoxides, and gamma-butenolides with high optical purities from readily-available starting materials by using environmentally-suitable materials such as bakers' yeast and hydrolysis enzyme, lipase.. Furthermore, plant conservation materials such as insect pheromones and plant hormones, medicines, and their key-intermediates were synthesized from products described above, and biological activities of their synthesized materials are under investigaiton. Major results are summarized as follows :1. Optically active malic acid, which is a useful key-intermediate in the synthesis of natural products, was synthesized.2. Optically active 3-chloro-2-hydroxyalkanoates were synthesized, and the total synthesis of (-) -disparlure was established.3. Both enantiomers of gamma-butenolides were synthesized with high selectivity, and these were applied for the syntheses of (3aS,6aS) -ethysolide, whisky lactone, and (-) -avenaciolide.4. Optically active alpha-hydroxyaldehydes and glycidic esters, which are useful key-intermediates for the synthesis of pestalotin, accelating the growth of plants, were synthesized.5. Flourine analog of methyl (Z) -5-tetradecenoate, a sex pheromone of soybean beetle was synthesized.

在这个项目中，我们使用面包酵母和水解酶、脂肪酶等环保材料，成功地从易于获得的起始原料中合成了高光学纯度的手性醇、环氧化物和γ-丁烯内酯。由上述产品合成了昆虫信息素和植物激素等保护材料、药物及其关键中间体，其合成材料的生物活性正在研究中。调查。主要研究结果如下： 1．合成了光学活性苹果酸，它是合成天然产物的重要中间体。 2．合成了光学活性的3-氯-2-羟基链烷酸酯，并建立了(-)-disparlure的全合成方法。 3．高选择性地合成了γ-丁烯内酯的两种对映体，并应用于(3aS，6aS)-乙基固体、威士忌内酯和(-)-燕麦内酯的合成。 4．合成了光学活性的α-羟基醛和缩水甘油酯，它们是合成培斯洛汀、促进植物生长的重要中间体。 5．合成了大豆甲虫性信息素(Z)-5-十四烯酸甲酯的氟类似物。

项目成果

坪井貞夫: "Lipase-catalyzed kinetic resolution of 3-chloro-2-hydroxyalkanoates.Its application for the synthesis of (-) -disparlure" Tetrahedron : Asymmetry. 8. 375-379 (1997)

Sadao Tsuboi：“脂肪酶催化的 3-氯-2-羟基链烷酸酯的动力学拆分。其在 (-)-disparlure 合成中的应用”四面体：不对称性。8. 375-379 (1997)

Sadao Tsuboi, Nobuyuki Yamafuji, and Masanori Utaka: "Lipase-catalyzed kinetic resolution of 3-chloro-2-hydroxyalkanoates. Its application for the synthesis of (-) -disparlure" Tetrahedron : Asymmetry. Vo.8 (No.3). 375-379 (1997)

Sadao Tsuboi、Nobuyuki Yamafuji 和 Masanori Utaka：“脂肪酶催化的 3-氯-2-羟基链烷酸酯的动力学拆分。其在 (-)-disparlure 合成中的应用”四面体：不对称性。

Sadao Tsuboi, Shin-ichiro Ono, and Masanori Utaka: "Aymmetric Synthesis of Optically Active Malic Acid" J.Fac.Environ.Sci.and Tech., Okayama Univ.Vol.1 (No.1). 205-210 (1996)

Sadao Tsuboi、Shin-ichiro Ono 和 Masanori Utaka：“光学活性苹果酸的不对称合成”J.Fac.Environ.Sci.and Tech.，冈山大学第 1 卷（第 1 期）。

坪井貞夫: "Asymmetric Synthesis of Optically Active Malic Afid" J.Fac.Environ.Sci.and Tech.,Okayama Univ.1. 205-210 (1996)

Sadao Tsuboi：“光学活性苹果酸 Afid 的不对称合成”J.Fac.Environ.Sci.and Tech.，冈山大学 1 205-210 (1996)。

坪井貞夫: "C : Pase-Catalyzed kinetic resolution of 3-chlors-2-hydroxy-alkanoates. Its application for the synthesis of (-)-disparlure" Tetrahedron Aeymmetry. 8(印刷中). (1997)

Sadao Tsuboi：“C：3-氯-2-羟基链烷酸酯的 Pase 催化动力学拆分。其在 (-)-disparlure 合成中的应用”Tetrahedron Aeymmetry 8（出版中）。