Development of microwave-assisted thermal electrocyclic reaction of an 67π-azahexatriene system and the applied to synthesis of bioactivity natural products

67π-氮杂六三烯体系微波辅助热电循环反应的研究进展及其在生物活性天然产物合成中的应用

• 批准号: 15590033
• 负责人: CHOSHI Tominari
• 金额: $ 2.11万
• 依托单位: Fukuyama University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (C)
• 财政年份: 2003
• 资助国家: 日本
• 起止时间: 2003 至 2005
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-15590033/
• 关键词: microwave; electrocyclic reaction; 1-azahexatriene; isoquinoline; TMC-120A, B, and C; bicolorine; trospheridine; scorpinone; benzo[c]isoquinoline; azaanthraquinone; nitroisoquinoline; methoxyisoquinoline; TMC-120A, B, and C; furo[3,2-h]isoqui

Features of the microwave-assisted organic reaction are that the reproducibility is high in order to uniformly heat in reaction system. In the pericyclic reaction, its application to Diels-Alder reaction and Claisen rearrangement reaction was examined. However, that application to the electrocyclic reaction was not yet reported.We have examined the efficient synthesis of biological activity heterocyclic compounds through a construction of isoquinoline based on a microwave-assisted thermal electrocyclic reaction of an 6π-electrocn system.(1)Effect of microwave to thermal electrocyclic reaction of azahexatriene system(2)Synthesis of the new furo[3,2-h]isoquinoline alkaloid, TMC-120A, B, and C possessing inhibitory activity against the interleukin-5.(3)Synthetic study of phenanthridine alkaloid, trispheridine(4)Synthetic study of azaanthraquinone alkaloid, scorpinoneWe established the new synthetic method of isoquinolines based on a microwave-assisted thermal electrocyclic reaction. This method was applied, and the total. synthesis of the furo[3,2-h]isoquinoline alkaloid, TMC-120A,B,C, phenanthridine alkaloid, trispheridine, and azaanthraquinone alkaloid, scorpinone were achieved.

微波辅助有机反应的特点是再现性高，以便在反应体系中均匀加热。在周环反应中，考察了它在Diels-Alder反应和Claisen重排反应中的应用。我们研究了微波辅助6π-电环体系的热电环化反应，通过构建异喹啉，有效地合成具有生物活性的杂环化合物。（1）微波对氮杂己三烯体系热电环化反应的影响（2）具有白细胞介素5抑制活性的呋喃并[3，2-h]异喹啉生物碱TMC-120 A、B和C的合成。（3）菲啶类生物碱三球吡啶的合成研究（4）氮杂蒽醌类生物碱蝎品酮的合成研究我们建立了微波辅助电热环化反应合成异喹啉类化合物的新方法。这种方法被应用，并总。合成了呋喃并[3，2-h]异喹啉类生物碱TMC-120 A、B、C、菲啶类生物碱三色堇定和氮杂蒽醌类生物碱蝎品酮。

项目成果

A total synthesis of a new type of furo {3,2-h}isoquinoline alkaloid. TMC-120B

新型呋喃{3,2-h}异喹啉生物碱的全合成。

• 发表时间: 2003
• 期刊: Heterocycles 61
• 作者: T.Kumemura;T.Choshi;A.Hirata;M.Sera;Y.Takahashi;J.Nobuhiro;S.Hibino
• 通讯作者: S.Hibino

A highly efficient synthesis of trispheridine through a construction of tetrahydro-phenanthridine based on a microwave-assisted thermal electrocyclic reaction of an aza 6π-electron system

基于氮杂6π电子体系的微波辅助热电环反应构建四氢菲啶高效合成三川啶

• 发表时间: 2005
• 期刊: Heterocycles 66
• 作者: T.Kumemura;T.Choshi;J.Yukawa;A.Hirose;J.Nobuhiro;S.Hibino
• 通讯作者: S.Hibino

Synthesis of the new furo[3,2-h]isoquinoline alkaloid, TMC-120B from Aspergillus ustus

• DOI: 10.1248/cpb.53.393
• 发表时间: 2005-04-01
• 期刊: CHEMICAL & PHARMACEUTICAL BULLETIN
• 影响因子: 1.7
• 作者: Kumemura, T;Choshi, T;Hibino, S
• 通讯作者: Hibino, S

T.Choshi et al.: "A TOTAL SYNTHESIS OF A NEW TYPE OF FURO[3,2-h]ISOQUINOLINE ALKALOID, TMC-120B"Heterocycles. 61. 13-17 (2003)

T.Choshi 等人：“新型呋喃[3,2-h]异喹啉生物碱，TMC-120B 的全合成”杂环化合物。

A highly efficient synthesis of trispheridine through a construction of letrahydrophenanthridine based on a microwave-assisted thermal electrocyclic reaction of an aza 6π-electron system

基于氮杂6π电子体系的微波辅助热电环反应构建四氢菲啶高效合成三川啶

• 发表时间: 2005
• 期刊: Heterocycles 66
• 作者: T.Kumemura;T.Choshi;J.Yukawa;A.Hirose;J.Nobuhiro;S.Hibino
• 通讯作者: S.Hibino