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

被引：15
|
作者：
Bian, Jinlei [1 ,3 ]
Deng, Bang [1 ,3 ]
Zhang, Xiaojin [1 ,4 ]
Hu, Tianhan [3 ]
Wang, Nan [3 ]
Wang, Wei [3 ]
Pei, Haixiang [3 ]
Xu, Yu [3 ]
Chu, Hongxi [1 ,3 ]
Li, Xiang [1 ]
Sun, Haopeng [1 ,3 ]
You, Qidong [1 ,2 ,3 ]
机构：
[1] China Pharmaceut Univ, Jiangsu Key Lab Drug Design & Optimizat, Nanjing 210009, Jiangsu, Peoples R China
[2] China Pharmaceut Univ, State Key Lab Nat Med, Nanjing 210009, Jiangsu, Peoples R China
[3] China Pharmaceut Univ, Sch Pharm, Dept Med Chem, Nanjing 210009, Jiangsu, Peoples R China
[4] China Pharmaceut Univ, Sch Sci, Dept Organ Chem, Nanjing 210009, Jiangsu, Peoples R China
来源：
TETRAHEDRON LETTERS | 2014年 / 55卷 / 08期
基金：
中国国家自然科学基金;
关键词：
beta-Lapachone; Lewis acid; Intramolecular cyclization; Regioselective Quinone; TRYPANOSOMA-CRUZI; C-O; DERIVATIVES; NQO1;
D O I：
10.1016/j.tetlet.2014.01.059
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly regioselective intramolecular cyclization of lapachol mediated by Lewis acids including NbCl5, AlCl3, and FeCl3 was developed for synthesizing beta-lapachone in excellent yields without any formation of the isomer alpha-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 alpha-lapachone as the main product. A possible mechanism for the Lewis acid mediated cyclization was also discussed. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1475 / 1478
页数：4
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