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

共 38 条

[1]

[Anonymous], 2005, ANGEW CHEM

[2] Direct Mannich and nitro-Mannich reactions with non-activated imines:: AgOTf-catalyzed addition of pronucleophiles to ortho-alkynylaryl aldimines leading to 1,2-dihydroisoquinolines [J].

Asao, N ;

Yudha, S ;

Nogami, T ;

Yamamoto, Y .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (34) :5526-5528

[3] An environmentally friendly synthetic method of 1,2-dihydroisoquinoline frameworks via three-component reaction with o-alkynylbenzaldehydes, primary amines, and pronucleophiles [J].

Asao, Naoki ;

Iso, Kentaro ;

Yudha S., Salprima .

ORGANIC LETTERS, 2006, 8 (18) :4149-4151

[4] The palladium-catalyzed C-H activation of benzylic gem-dialkyl groups [J].

Baudoin, O ;

Herrbach, A ;

Guéritte, F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (46) :5736-5740

[5]

Baudoin O., 2003, ANGEW CHEM, V115, P5914

[6] β-Phenylethylamines and the isoquinoline alkaloids [J].

Bentley, Kenneth W. .

NATURAL PRODUCT REPORTS, 2006, 23 (03) :444-463

[7] ALKALOIDS IN ANIMAL AND HUMAN TISSUES .6. SYNTHESIS AND ABSOLUTE-CONFIGURATION OF CHIRAL 2,3,10,11-TETRAHYDROXY-8-METHYL-BERBINES [3] [J].

BRUDERER, H ;

METZGER, J ;

BROSSI, A ;

DALY, JJ .

HELVETICA CHIMICA ACTA, 1976, 59 (08) :2793-2807

[8] Peripheral benzodiazepine receptors and mitochondrial function [J].

Casellas, P ;

Galiegue, S ;

Basile, AS .

NEUROCHEMISTRY INTERNATIONAL, 2002, 40 (06) :475-486

[9] Synthesis of Benzocyclobutenes by Palladium-Catalyzed C-H Activation of Methyl Groups: Method and Mechanistic Study [J].

Chaumontet, Manon ;

Piccardi, Riccardo ;

Audic, Nicolas ;

Hitce, Julien ;

Peglion, Jean-Louis ;

Clot, Eric ;

Baudoin, Olivier .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (45) :15157-15166

[10] Asymmetric synthesis of isoquinoline alkaloids [J].

Chrzanowska, M ;

Rozwadowska, MD .

CHEMICAL REVIEWS, 2004, 104 (07) :3341-3370

← 1 2 3 4 →