Synthesis of 3,4-Dihydroisoquinolines by a C(sp3)-H Activation/Electrocyclization Strategy: Total Synthesis of Coralydine

被引：101

作者：

Chaumontet, Manon ^{[2
]}

Piccardi, Riccardo ^{[1
]}

Baudoin, Olivier ^{[1
]}

机构：

[1] Univ Lyon 1, Inst Chim & Biochim Mol & Supermol, CNRS UMR5246, F-69622 Villeurbanne, France

[2] CNRS UPR2301, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 01期

关键词：

alkaloids; C-H activation; electrocyclic reactions; heterocycles; natural products; TANDEM NUCLEOPHILIC-ADDITION; C-H ACTIVATION; ISOQUINOLINE ALKALOIDS; HETEROCYCLIC-COMPOUNDS; 1,2-DIHYDROISOQUINOLINES; BENZOCYCLOBUTENES; THERMOLYSIS; CYCLIZATION; ACCESS; PRONUCLEOPHILES;

D O I：

10.1002/anie.200804444

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Thanks to C-H activation: 3-Aryl-3,4-dihydroisoquinolines (2) are synthesized from bromobenzenes (1) by a sequence comprising a C(sp3)-H activation, a Curtius rearrangement, and a tandem electrocyclic ring-opening/6π electrocyclization. This method is applied to the synthesis of various isoquinoline-containing molecules, including the tetrahydroprotoberberine alkaloid coralydine. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：179 / 182

页数：4

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