Total synthesis of rhein and diacerhein via a directed ortho metalation of an aromatic substrate

被引：29

作者：

Gonnot, Vanessa

Tisserand, Steve

Nicolas, Marc

Baati, Rachid

Mioskowski, Charles

机构：

[1] Univ Strasbourg 1, Fac Pharm, Synth Bio Organ, F-67401 Illkirch Graffenstaden 67401, France

[2] Labs Pierre Fabre, F-81600 Gaillac, France

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 40期

关键词：

directed ortho metalation; anthraquinone; rhein; diacerhein;

D O I：

10.1016/j.tetlet.2007.07.218

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient total synthesis of rhein and diacerhein has been accomplished by relying on a remarkable regioselective directed ortho metalation (DOM) followed by a one-pot two step addition-cyclization reaction, generating phthalide 5 intermediate efficiently. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：7117 / 7119

页数：3

共 26 条

[1] PREPARATION OF FUNCTIONALIZED JUGLONE ACETATES AND JUGLONES VIA 1,4-DIMETHOXYNAPHTHALENE DERIVATIVES - SYNTHESIS OF ANTHRAQUINONES RELATED TO RHEIN AND ALOE EMODIN [J].