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Effective Preparation of Valuable Biologically Active Compounds Employing Catalytic Construction of Polycyclic Ring System

利用多环体系催化构建有效制备有价值的生物活性化合物

基本信息

批准号：
17390003
负责人：
IHARA Masataka
金额：
$ 9.47万
依托单位：
Hoshi University (2006)Tohoku University (2005)
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (B)
财政年份：
2005
资助国家：
日本
起止时间：
2005 至 2006
项目状态：
已结题

项目摘要

When various functional groups exist on a polycyclic skeleton, the three-dimensional relationships of the functional groups are restricted and a specific biological activity would be expected due to the rigid conformation. Therefore, the development of an efficient method for the construction of polycyclic ring systems is highly desired, particularly in the field of medicinal chemistry.Cascade reactions are useful methods for the construction of polycyclic skeletons, which are important cores for biological activities. A variety of cascade reactions, carried out under multiple reaction conditions, such as pericyclic, polar, radical, and transition metal-catalyzed reaction conditions, have been investigated.Culmorin, pentalenene, pentalenic acid, deoxypentalenic acid, longiborneol, cedrandiol, 8, 14-cedranoxide, atisirene, atisine, and estrane-type steroids were synthesized via the intramolecular double Michael reaction. Aza double Michael reaction was applied to the syntheses of tylophorine, epilupinine, tacamonine, and paroxetine. Furthermore, sequential Michael and aldol reactions were performed in both intramolecular and intermolecular manners, leading to the formation of polycyclic compounds fused to a four-membered ring. Synthesis of paesslerin A utilizing a multicomponent cascade reaction revealed an error in the proposed structure.Unique cascade reactions, performed under radical and transition metal-catalyzed reaction conditions, were also investigated. With the combination of several cascade reactions, serofendic acids and methyl 7β-hydroxykaurenoate, both of which have neuroprotective activity, were synthesized in a selective manner.

当多环骨架上存在各种官能团时，官能团的三维关系受到限制，由于刚性构象，可能会产生特定的生物活性。因此，开发一种高效的构建多环环体系的方法是非常必要的，特别是在药物化学领域。级联反应是构建多环骨架的有用方法，而多环骨架是生物活性的重要核心。通过分子内双Michael反应合成了库莫林、五茂烯、五烯酸、脱氧戊烯酸、长冰片、雪松二醇、8，14-雪松、环丁烯和雌烷型甾体。将氮杂双迈克尔反应应用于苯丙氨酸、淫羊藿碱、他卡莫宁和帕罗西汀的合成。此外，连续的Michael和Aldol反应在分子内和分子间进行，导致形成融合成四元环的多环化合物。利用多组分级联反应合成了巴斯莱素A，发现了所提出的结构中的错误。还研究了在自由基和过渡金属催化的反应条件下进行的独特的级联反应。通过几个级联反应的结合，选择性地合成了具有神经保护活性的血清烯酸甲酯和7-β-羟基奎宁酸甲酯。

项目成果

期刊论文数量（0）

专著数量（0）

科研奖励数量（0）

会议论文数量（0）

专利数量（0）

Palladium-catalyzed carbon dioxide elimination-fixation reaction of 6-methoxycarbonyloxy-2, 4-hexadien-1-ols.

钯催化的 6-甲氧基羰氧基-2, 4-己二烯-1-醇的二氧化碳消除固定反应。

DOI：
发表时间：
2006
期刊：
Tetrahedron 62
影响因子：
0
作者：
Kazato Inanaga;Kiyosei Takasu;Masataka Ihara;Kiyosei Takasu 他2名;Kiyosei Takasu 他3名;Kiyosei Takasu 他6名;Kiyosei Takasu 他4名;Yamagishi K.;Yamagishi K.;Masahiro Yoshida;Masahiro Yoshida;Masahiro Yoshida
通讯作者：
Masahiro Yoshida

Synthesis of Medium-Sized Cyclic γ-Haloketones by Radical Mediated Ring-Opening Reaction of Lewis Acid of Lewis Acid Catalyzed(2+2)-Cycloaddition Product

路易斯酸催化(2+2)-环加成产物自由基介导的路易斯酸开环反应合成中型环状γ-卤代酮