Lewis acid mediated highly regioselective intramolecular cyclization for the synthesis of 尾-lapachone

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• 作者：Jinlei Bian ; Bang Deng ; Xiaojin Zhang ; Tianhan Hu ; Nan Wang ; Wei Wang ; Haixiang Pei ; Yu Xu ; Hongxi Chu ; Xiang Li ; Haopeng Sun ; Qidong You
• 关键词：尾-Lapachone ; Lewis acid ; Intramolecular cyclization ; Regioselective ; Quinone
• 刊名：Tetrahedron Letters
• 出版年：19 February, 2014
• 年：2014
• 卷：55
• 期：8
• 页码：1475-1478
• 全文大小：491 K

文摘

A highly regioselective intramolecular cyclization of lapachol mediated by Lewis acids including NbCl₅, AlCl₃, and FeCl₃ was developed for synthesizing 尾-lapachone in excellent yields without any formation of the isomer 伪-lapachone. This procedure was efficient, mild, and easily scalable that avoided using highly hazardous concd H₂SO₄. In the case of ZrCl₄ the cyclization was found to give 伪-lapachone as the main product. A possible mechanism for the Lewis acid mediated cyclization was also discussed.