Novel synthesis of indole derivatives based on the palladium catalyzed cross-coupling reaction with indolylborates as a key reaction

以吲哚硼酸酯为关键反应的钯催化交叉偶联反应新合成吲哚衍生物

• 批准号: 09672151
• 负责人: ISHIKURA Minoru
• 金额: $ 1.98万
• 依托单位: Health Sciences University of Hokkaido
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (C)
• 财政年份: 1997
• 资助国家: 日本
• 起止时间: 1997 至 1999
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-09672151/
• 关键词: indolylborate; indole; borate; cross-coupling reaction; ellipticine; yuehchukene; 生物活性物質; パラジウム触媒; エリプチシン; yuehchukene; 一酸化炭素; インドール誘導体; アレニルインドール

Indolylborates, readily available from the corresponding 2-lithioindoles and triethylborane in situ, are valuable synthetic intermediates, and the development of their synthetic capabilities has been our continuing interest. During these studies, the palladium catalyzed cross-coupling reaction with indolylborates has been proven to be an effective protocol for the preparation of substituted indole derivatives. In these studies, the followings have been achieved by the use of the cross-coupling reaction as a key reaction;1. Synthesis of ellipticine and its analogues by the palladium catalyzed tandem cyclization cross-coupling reaction2. Synthesis of yuehchukene and its analogues by the palladium catalyzed carbonylative cross-coupling reaction.

吲哚基硼酸酯，容易从相应的2-锂吲哚和三乙基硼烷原位，是有价值的合成中间体，和他们的合成能力的发展一直是我们的持续兴趣。在这些研究中，钯催化的吲哚硼酸酯的交叉偶联反应已被证明是制备取代吲哚衍生物的有效方案。在这些研究中，通过使用交叉偶联反应作为关键反应，取得了以下成果：1。钯催化串联环化偶联反应合成椭圆藤碱及其类似物2。钯催化的羰基交叉偶联反应合成越竹烯及其类似物。

项目成果

石倉 稔: "The use of the N-substituted triethylcindol-2-yl)borate for the palladium catalyzed cross-coupling reaction" Heterocycles. 45(12). 2309-2312 (1997)

Minoru Ishikura：“N-取代的三乙基吲哚-2-基)硼酸酯在钯催化的交叉偶联反应中的用途”杂环化合物45(12) (1997)。

Minoru Ishikura, Lsao Agata, and Nobuya Katagiri: "Investigation of the reaction of N-substituted indolylborates: Palladium catalyzed cross-coupling reactions and intramolecular alkyl migration reactions"J. Heterocyclic Chem.. 36. 873-879 (1999)

Minoru Ishikura、Lsao Agata 和 Nobuya Katagiri：“N-取代吲哚基硼酸酯的反应研究：钯催化的交叉偶联反应和分子内烷基迁移反应”J。

Minoru Ishikura, Ayako Hino; and Nobuya Katagiri: "An efficient synthesis of ellipticine"Heterocycles. 53. 11-14 (2000)

石仓稔、日野绫子；

Minoru Ishikura: "Total Synthesis of Yuehchukene"Heterocycles. 53. 553-556 (2000)

Minoru Ishikura：“Yuehchukene的全合成”杂环。

Minoru Ishikura, Toshikatsu Yaginuma, Isao Agata, Yoshihisa Miwa, Reiko Yanada, and Tooru Taga: Synlett. 214-216 (1997)

Minoru Ishikura、Toshikatsu Yaginuma、Isao Agata、Yoshihisa Miwa、Reiko Yanada 和 Toru Taga：Synlett。