Synthesis of the bicyclic welwitindolinone core via an alkylation/cyclization cascade reaction.

Synthesis of the bicyclic welwitindolinone core via an alkylation/cyclization cascade reaction.
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DOI:
10.1021/ol902173g
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发表时间:
2009-11-19
期刊:
影响因子:
5.2
通讯作者:
Shea KJ
Shea KJ
中科院分区:
化学1区
文献类型:
--
作者:
Brailsford JA;Lauchli R;Shea KJ

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据报道,通过烷基化/环化反应合成了先进的 welwitindolinone 中间体。关键步骤涉及甲硅烷基乙烯酮缩醛胺与呋喃醇的一锅路易斯酸介导的烷基化,然后进行分子内环化。该反应是立体选择性的并且在低温下发生。该环加合物是高度官能化的并且包含welwitindolinone核心结构。
Synthesis of an advanced welwitindolinone intermediate via an alkylation/cyclization reaction is reported. The key step involves a one pot Lewis acid mediated alkylation of a silylketene aminal with a furan alcohol followed by an intramolecular cyclization. The reaction is stereoselective and takes place at low temperature. The cycloadduct is highly functionalized and contains the welwitindolinone core structure.
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