Concise and Diversity-Oriented Route toward Polysubstituted 2-Aminoimidazole Alkaloids and Their Analogues

被引：143

作者：

Ermolat'ev, Denis S. ^{[1
]}

Bariwal, Jitender B. ^{[1
]}

Steenackers, Hans P. L. ^{[2
]}

De Keersmaecker, Sigrid C. J. ^{[2
]}

Van der Eycken, Erik V. ^{[1
]}

机构：

[1] Katholieke Univ Leuven, Lab Organ & Microwave Assisted Chem, B-3001 Louvain, Belgium

[2] Katholieke Univ Leuven, Ctr Microbial & Plant Genet, B-3001 Louvain, Belgium

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 49期

关键词：

alkaloids; 2-aminoimidazoles; cyclization; heterocycles; natural products; MICROWAVE-ASSISTED SYNTHESIS; HOMOGENEOUS GOLD CATALYSIS; IMIDAZOLE ALKALOIDS; HYDROAMINATION; HETEROCYCLES; CARBOCYCLES; ALKENES; ALKYNES; LIBRARY;

D O I：

10.1002/anie.201004256

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Alkaloids of the naamine family were synthesized from diverse propargylamines in just two steps (see scheme: R1=Me, R 2=substituted benzyl, R3=Ar). Thus, the addition to a propargylamine of a carbodiimide generated in situ, silver(I)-catalyzed intramolecular hydroamidation, and subsquent deprotection provide access to the heterocyclic core of numerous natural products and biologically active compounds. Boc=tert-butoxycarbonyl, Cbz=carbobenzyloxy. Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：9465 / 9468

页数：4

共 28 条

[1] A concise total synthesis of naamidine A [J].

Aberle, NS ;

Lessene, G ;

Watson, KG .

ORGANIC LETTERS, 2006, 8 (03) :419-421

[2] Synthesis and Antibiofilm Activity of a Second-Generation Reverse-Amide Oroidin Library: A Structure-Activity Relationship Study [J].

Ballard, T. Eric ;

Richards, Justin J. ;

Wolfe, Amanda L. ;

Melander, Christian .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (34) :10745-10761

[3] Efficient Microwave-Assisted Synthesis of Secondary Alkylpropargylamines by Using A3-Coupling with Primary Aliphatic Amines [J].

Bariwal, Jitender B. ;

Ermolat'ev, Denis S. ;

Van der Eyeken, Erik V. .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (11) :3281-3284

[4] A Direct and Efficient Total Synthesis of the Tubulin-Binding Agents Ceratamine A and B; Use of IBX for a Remarkable Heterocycle Dehydrogenation [J].

Coleman, Robert S. ;

Campbell, Erica L. ;

Carper, Daniel J. .

ORGANIC LETTERS, 2009, 11 (10) :2133-2136

[5]

Eilrich G. L., 1975, [No title captured], Patent No. [US-3904395, 3904395]

[6] Concise microwave-assisted synthesis of 2-aminoimidazole marine sponge alkaloids of the isonaamines series [J].

Ermolat'ev, D. S. ;

Alifanov, V. L. ;

Rybakov, V. B. ;

Babaev, E. V. ;

Van der Eycken, E. V. .

SYNTHESIS-STUTTGART, 2008, 13 (13) :2083-2088

[7]

Ermolat'ev D. S., 2008, THESIS KATHOLIEKE U

[8]

Giles R. L., 2009, ANGEW CHEM, V121, P3162

[9] Addition-Hydroamination Reactions of Propargyl Cyanamides: Rapid Access to Highly Substituted 2-Aminoimidazoles [J].

Giles, Robert L. ;

Sullivan, John D. ;

Steiner, Andrew M. ;

Looper, Ryan E. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (17) :3116-3120

[10] Synthesis of the pyrrole-imidazole alkaloids [J].

Hoffmann, H ;

Lindel, T .

SYNTHESIS-STUTTGART, 2003, (12) :1753-1783

← 1 2 3 →