Synthetic Studies on Spirolide, a Macrocyclic Alkaloid, having potential neurotoxicity

具有潜在神经毒性的大环生物碱螺环内酯的合成研究

• 批准号: 21590012
• 负责人: ISHIHARA Jun
• 金额: $ 3万
• 依托单位: Nagasaki University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (C)
• 财政年份: 2009
• 资助国家: 日本
• 起止时间: 2009 至 2011
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-21590012/
• 关键词: 合成化学; 全合成; 天然物; 海産毒; 天然物合成; Diels-Alder反応

Spirolide is a marine natural product, having strong neurotoxicity. The structure was featured by the macrocyclic framework containing the azaspirocyclic moiety and the bisspiroacetal. The absolute configuration at C-2 and C-4 has not been clarified, and the precise mode of action still remains unknown. We have studied the synthesis of this natural toxin to clarify the complete structure. The framework of the upper half fragment, having cyclohexene ring, was constructed by chiral templated Diels-Alder reaction and the lower half fragment, having spirocyclic system, was successfully synthesized.

螺内酯是一种海洋天然产物，具有很强的神经毒性。该结构的特点是由大环框架含有氮杂螺环部分和双螺缩醛。C-2和C-4的绝对构型尚未阐明，确切的作用方式仍然未知。我们已经研究了这种天然毒素的合成，以阐明完整的结构。通过手性模板Diels-Alder反应构建了上半部分含环己烯环的骨架，成功合成了下半部分含螺环体系的骨架。

项目成果

Synthesis and preliminary biological evaluation of 20-epi-eldecalcitol [20-epi-1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3: 20-epi-ED-71]

• DOI: 10.1016/j.jsbmb.2010.03.041
• 发表时间: 2010-07
• 期刊: The Journal of Steroid Biochemistry and Molecular Biology
• 作者: S. Hatakeyama;M. Yoshino;Kohei Eto;Keisuke Takahashi;Jun Ishihara;Y. Ono;H. Saito;N. Kubodera

インジウムを用いるReformatsky-Claisen転位反応の開発

使用铟开发 Reformatsky-Claisen 重排反应

• 发表时间: 2009
• 作者: 小山典子;西野幸宏;高橋圭介;石原淳;畑山範
• 通讯作者: 畑山範

New Variant of Reformasky-Claisen Rearrangement Mediated by Indium Chloride, 22^<nd>

由氯化铟介导的 Reformasky-Claisen 重排的新变体，22^<nd>

• 发表时间: 2011
• 作者: J. Ishihara;Y. Watanabe;N. Koyama;Y. Nishino;K. Takahashi;S. Hatakeyama
• 通讯作者: S. Hatakeyama

Synthetic study on clutiolide based on a remote chelation controlled Ireland-Claisen rearrangement.

基于远程螯合控制的爱尔兰-克莱森重排的曲草内酯的合成研究。

• 发表时间: 2010
• 期刊: Heterocycles 80
• 作者: J.Ishihara;O.Tokuda;K.Shiraishi;Y.Nishino;K.Takahashi;S.Hatakeyama
• 通讯作者: S.Hatakeyama

Organocatalytic asymmetric synthesis of quinine and quinidine

• DOI: 10.1016/j.tetlet.2010.12.066
• 发表时间: 2011-02
• 期刊: Tetrahedron Letters
• 影响因子: 1.8
• 作者: S. Sarkar;Yuko Taira;Ayako Nakano;Keisuske Takahashi;Jun Ishihara;S. Hatakeyama