Construction of dihydropyran-bridged macrocycles by inverse-electron-demand Diels-Alder reaction

被引：2

作者：

Dong, Xiaomei

Wang, Qingxia

Zhang, Qian

Xu, Shuai

Wang, Zhihong ^{[1
]}

机构：

[1] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China

来源：

TETRAHEDRON | 2013年 / 69卷 / 52期

基金：

中国国家自然科学基金;

关键词：

Dihydropyran-bridged macrocycles; Inverse-electron-demand Diels-Alder; reaction; Lewis acid catalysis; CATALYSTS; MACROCYCLIZATIONS; METATHESIS; LIBRARY; BINDING; DESIGN; DNA;

D O I：

10.1016/j.tet.2013.10.101

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of dihydropyran-bridged macrocyclic structures were constructed by the inverse-electron-demand Diels Alder reaction of 2-oxo-4-aryl-but-3-enoates. Controlling of the tether length and the position of the activating substituent in the substrates would guide the reaction to the formation of four different types of polycyclic frames, namely bicyclic [n.3.1], bicyclic [n.2.2], tricyclic [n.3.1.1], and tricyclic [n.2.2.2] macrocycles. The intermolecular/intramolecular selectivity of the Diels Alder reaction was virtually governed by the tether length. The reactions were carried out rapidly under mild conditions, and offered a practical method for creating bridged polycyclic structures with large rings from acyclic precursors. (C) 2013 Elsevier Ltd. All rights reserved.

引用

收藏

页码：11144 / 11154

页数：11

相关论文

共 29 条

[1] Diversity Oriented Synthesis of Pyran Based Polyfunctional Stereogenic Macrocyles and Their Conformational Studies [J].

Ajay, Arya ;

Sharma, Shrikant ;

Gupt, Munna Prasad ;

Bajpai, Vikas ;

Hamidullah ;

Kumar, Brijesh ;

Kaushik, Mahabir Prasad ;

Konwar, Rituraj ;

Ampapathi, Ravi Sankar ;

Tripathi, Rama Pati .

ORGANIC LETTERS, 2012, 14 (17) :4306-4309

[2]

Bear BR, 2001, ANGEW CHEM INT EDIT, V40, P821

[3] Strategies and Tactics for the Metal-Directed Synthesis of Rotaxanes, Knots, Catenanes, and Higher Order Links [J].

Beves, Jonathon E. ;

Blight, Barry A. ;

Campbell, Christopher J. ;

Leigh, David A. ;

McBurney, Roy T. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (40) :9260-9327

[4] Efficient fluorescence enhancement and cooperative binding of an organic dye in a supra-biomolecular host-protein assembly [J].

Bhasikuttan, Achikanath C. ;

Mohanty, Jyotirmayee ;

Nau, Werner M. ;

Pal, Haridas .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (22) :4120-4122

[5] Enantioselective synthesis of bridged bicyclic ring systems [J].

Brailsford, John A. ;

Zhu, Liang ;

Loo, Mandy ;

Shea, Kenneth J. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (24) :9402-9405

[6] Template macrolactonization of trichloroethyl ester derivatives catalyzed by potassium salts [J].

Burke, SD ;

McDermott, TS ;

O'Donnell, CJ .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08) :2715-2718

[7] Dual function catalysts.: Dehydrogenation and asymmetric intramolecular Diels-Alder cycloaddition of N-hydroxy formate esters and hydroxamic acids:: Evidence for a ruthenium-acylnitroso intermediate [J].

Chow, CP ;

Shea, KJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (11) :3678-3679

[8] Origins of Regio- and Stereochemistry in Type 2 Intramolecular N-Acylnitroso Diels-Alder Reactions: A Computational Study of Tether Length and Substituent Effects [J].

Cleary, Leah ;

Mak, Victor W. ;

Rychnovsky, Scott D. ;

Shea, Kenneth J. ;

Sizemore, Nicholas .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (08) :4090-4098

[9] Microwave Assisted Synthesis of Bridgehead Alkenes [J].

Cleary, Leah ;

Yoo, Hoseong ;

Shea, Kenneth J. .

ORGANIC LETTERS, 2011, 13 (07) :1781-1783

[10] Macrocyclizations for Medicinal Chemistry: Synthesis of Druglike Macrocycles by High-Concentration Ullmann Coupling [J].

Collins, James C. ;

Farley, Kathleen A. ;

Limberakis, Chris ;

Liras, Spiros ;

Price, David ;

James, Keith .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (24) :11079-11090