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Systematic Synthesis of Bioactive Compounds Using Photochemical Method

光化学法系统合成生物活性化合物

基本信息

批准号：
12650846
负责人：
CHIBA Kazuhiro
金额：
$ 2.37万
依托单位：
Tokyo University of Agriculture and Technology
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (C)
财政年份：
2000
资助国家：
日本
起止时间：
2000 至 2002
项目状态：
已结题

项目摘要

Euglobal and robustadials were isolated from Encalyptus spp. as inhibitors of the Epstein-Barr virus activation, or as antimalarial compounds. Previously we reported an electrochemical generation of o-quinomethane and their cycloaddition with α-phellandrene to yield the euglobal Ia_1 and Ia_2 skeletons. Furthermore, the first, concise synthesis of natural euglobals has been accomplished by biomimetic cycloaddition of monotermpenes and quinomethanes generated in situ by oxidation of grandinol. In this paper, we introduced novel thermomorphic reaction systems that enable high-throughput synthesis of eublobal and robustadial skeletons via intermolecular hetero Diels-Alder reaction of terpenes and anodically generatefd o-quinomethanes.the thermomorphic liquid-liquid separation system composed of organic solvents of different polarity might allow for extremely efficient reactions, for example, by the association of apolar products and polar substrates or catalysts in a one-phase solution, w … More hich could be spatially separated after the completion of reactions. It should further open the door for the construction of liquid-phase combinatorial chemistry, industrial and green chemistry by the ease of the separation of products, catalyses, reagents, electrolytes, and/or soluble platforms for organic synthesis. This gave us the incentive to explore a novel thermomorphic reaction system using typical organis solvents. Among numerous compositions of organic solvents, an appropriate mixture of cyclohexane (CH) and nitroalkane (NA) was initially found to show the desired function, that is, a 75 : 25 (v/v) mixture of CH and NA [a 20 : 80 v/v mixture of nitromethane (NM) and nitroethane (NE)]. At 25℃, the solvent mixture was separated into an upper CH(main) phase and a lower NA(main) phase. temperature with an increase in the CH ratio to complete the one-phase formation. By using this system, several euglobal and robustadial skeletons could be synthesized just by changing alkenes (dienophiles for intermolecular hetero-Diels-Alder reaction), and most of the products were isolated from upper layer just by cooling to form the biphasic solution system after the completion of the reaction. Less

Euglobal和robustadials分离自Encalyptus spp.作为EB病毒活化的抑制剂，或作为抗疟疾化合物。以前我们报道了邻醌甲烷的电化学生成及其与α-水芹烯的环加成反应，得到了具有整体骨架的Ia_1和Ia_2。此外，第一个，简洁的天然优球蛋白的合成已经完成了仿生环加成反应的单萜和醌甲烷原位氧化的grandinol。本文介绍了一种新的热态反应体系，该体系可以通过萜烯和阳极生成的邻醌甲烷的分子间杂Diels-Alder反应高通量地合成稠环和稠环骨架。由不同极性的有机溶剂组成的热态液-液分离体系可以进行非常有效的反应，例如，通过在单相溶液中缔合非极性产物和极性底物或催化剂， ...更多信息其可以在反应完成后在空间上分离。它将进一步为液相组合化学、工业化学和绿色化学的构建打开大门，使有机合成的产物、催化剂、试剂、电解质和/或可溶性平台易于分离。这给了我们探索一种新的热晶化反应体系的动力，使用典型的有机溶剂。在众多的有机溶剂组合物中，最初发现环己烷（CH）和硝基烷烃（NA）的适当混合物显示出所需的功能，即CH和NA的75：25（v/v）混合物[硝基甲烷（NM）和硝基乙烷（NE）的20：80 v/v混合物]。在25℃下，将溶剂混合物分离为上部CH（主）相和下部NA（主）相。随着CH比率的增加，温度升高以完成单相形成。利用该体系，只需改变烯烃（分子间异Diels-桤木反应的亲双烯体）即可合成多个整球、健壮的骨架，反应完成后，大部分产物只需冷却即可从上层分离出来，形成两相溶液体系。少