Synthetic strategy toward skeletal diversity via solid-supported, Otherwise unstable reactive intermediates

被引:62
作者
Taylor, SJ
Taylor, AM
Schreiber, SL
机构
[1] Harvard Univ, Howard Hughes Med Inst, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
[2] Harvard Univ, ICCB, Cambridge, MA 02138 USA
关键词
diversity-oriented synthesis; enamines; nitrogen heterocycles; reactive intermediates; solid-phase synthesis;
D O I
10.1002/anie.200353466
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Solid supports lend stability: Skeletally diverse alkaloid-like compounds were obtained in only three steps from simple starting materials through a strategy based on dihydropyridine and dihydroisoquinoline intermediates supported on macrobeads (see picture). The otherwise unstable enamine double bond present in the intermediates can undergo a variety of transformations, including cycloadditions, selective reductions, and alkylations.
引用
收藏
页码:1681 / 1685
页数:5
相关论文
共 46 条
[1]   MONOCYCLIC ANTIBIOTIC BETA-LACTAMS [J].
ABDULLA, RF ;
FUHR, KH .
JOURNAL OF MEDICINAL CHEMISTRY, 1975, 18 (06) :625-627
[2]   ADDITION-REACTIONS OF HETEROCYCLIC-COMPOUNDS .56. FORMATION OF 1,2-DIHYDROAZOCINES FROM 1,2-DIHYDROPYRIDINES WITH DIMETHYL ACETYLENEDICARBOXYLATE [J].
ACHESON, RM ;
PAGLIETTI, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (21) :2496-2500
[3]   RING EXPANSION REACTIONS OF ISOQUINOLINE DERIVATIVES TO 2-BENZAZOCINE AND 3-BENZAZECINE DERIVATIVES [J].
BAMATRAF, MMM ;
VERNON, JM ;
WILSON, GD .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (13) :1647-1648
[4]   Expanding the functional group compatibility of small-molecule microarrays: Discovery of novel calmodulin ligands [J].
Barnes-Seeman, D ;
Park, SB ;
Koehler, AN ;
Schreiber, SL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (21) :2376-2379
[5]  
BARNESSEEMAN D, 2003, ANGEW CHEM, V115, P2478
[6]   Efficient robotic synthesis. Multi-component preparation of a tricyclic template by solid phase Tsuge reaction [J].
Bicknell, AJ ;
Hird, NW ;
Readshaw, SA .
TETRAHEDRON LETTERS, 1998, 39 (32) :5869-5872
[7]   A one-bead, one-stock solution approach to chemical genetics:: part 1 [J].
Blackwell, HE ;
Pérez, L ;
Stavenger, RA ;
Tallarico, JA ;
Eatough, EC ;
Foley, MA ;
Schreiber, SL .
CHEMISTRY & BIOLOGY, 2001, 8 (12) :1167-1182
[8]  
Breinbauer R, 2002, ANGEW CHEM INT EDIT, V41, P2879
[9]  
BREINBAUER R, 2002, ANGEW CHEM, V114, P3002
[10]  
Burke M. D., 2004, ANGEW CHEM, V116, P48