Diversity oriented synthesis: concise entry to novel derivatives of Yohimbine and Corynanthe alkaloids

被引：15
作者：
Wang, Zhiqian
Kaneda, Kyosuke
Fang, Zhenglai
Martin, Stephen F. [1 ]
机构：
[1] Univ Texas Austin, Dept Chem & Biochem, Austin, TX 78712 USA
来源：
TETRAHEDRON LETTERS | 2012年 / 53卷 / 05期
基金：
美国国家卫生研究院;
关键词：
Multicomponent assembly process; Imine; Dipolar cycloaddition; Suzuki reaction; N-Derivatization; HETEROCYCLIC SCAFFOLDS; MULTICOMPONENT REACTIONS; NATURAL-PRODUCTS; CHEMICAL SPACE; RECEPTORS; FACILE;
D O I：
10.1016/j.tetlet.2011.10.115
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel MCAP-cycloaddition sequence has been applied to the facile synthesis of p-carboline intermediates to gain rapid access to novel derivatives of Yohimbine-like and Corynanthe-like compounds that may be easily diversified by cross-coupling reactions and N-derivatizations to generate small compound libraries. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：477 / 479
页数：3
相关论文
共 23 条
[1]  
Boehringer M., 2004, U. S. Pat. Appl. Publ, Patent No. 2004259902
[2]  
Brown R. T., 1983, INDOLES
[3]   STEREOSPECIFIC SYNTHESIS OF THE (3A-ALPHA,11-ALPHA,12A-ALPHA)-DECAHYDROBENZO[A]PYRROLO[3,2-G]QUINOLIZINE RING-SYSTEM [J].
CLARK, RD ;
NELSON, JT ;
REPKE, DB .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1993, 30 (03) :829-831
[4]   STRUCTURE AFFINITY RELATIONSHIPS OF 12-SULFONYL DERIVATIVES OF 5,8,8A,9,10,11,12,12A,13,13A-DECAHYDRO-6H-ISOQUINO[2,1-G][1,6]NAPHTHYRIDINES AT ALPHA-ADRENOCEPTORS [J].
CLARK, RD ;
REPKE, DB ;
BERGER, J ;
NELSON, JT ;
KILPATRICK, AT ;
BROWN, CM ;
MACKINNON, AC ;
CLAGUE, RU ;
SPEDDING, M .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (02) :705-717
[5]   Synthesis and Diversification of 1,2,3-Triazole-Fused 1,4-Benzodiazepine Scaffolds [J].
Donald, James R. ;
Martin, Stephen F. .
ORGANIC LETTERS, 2011, 13 (05) :852-855
[6]   Binding of β-carbolines at imidazoline I2 receptors:: a structure-affinity investigation [J].
Glennon, RA ;
Grella, B ;
Tyacke, RJ ;
Lau, A ;
Westaway, J ;
Hudson, AL .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (04) :999-1002
[7]   Multicomponent Assembly Strategies for the Synthesis of Diverse Tetrahydroisoquinoline Scaffolds [J].
Granger, Brett A. ;
Kaneda, Kyosuke ;
Martin, Stephen F. .
ORGANIC LETTERS, 2011, 13 (17) :4542-4545
[8]   Multicomponent Assembly and Diversification of Novel Heterocyclic Scaffolds Derived from 2-Arylpiperidines [J].
Hardy, Simon ;
Martin, Stephen F. .
ORGANIC LETTERS, 2011, 13 (12) :3102-3105
[9]   On the Lewis acid-induced [1,3]-dipolar cycloaddition of allylic and homoallylic alcohols to N-methyl-C-phenyl nitrone [J].
Jones, AD ;
Knight, DW ;
Thornton, SR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (22) :3337-3344
[10]   SYNTHESIS AND ANTIHYPERTENSIVE ACTIVITY OF 2-BENZAMIDO-1,2,3,4,6,7,12,12B-OCTAHYDROINDOLO[2,3-A]QUINOLIZINES [J].
KLIOZE, SS ;
EHRGOTT, FJ ;
WILKER, JC ;
WOODWARD, DL .
JOURNAL OF MEDICINAL CHEMISTRY, 1979, 22 (12) :1497-1504
123