Reagent-controlled domino synthesis of skeletally-diverse compound collections

被引:42
作者
Waldmann, Herbert [1 ,2 ]
Kuehn, Marc [1 ,2 ]
Liu, Wei [1 ,2 ]
Kumar, Kamal [1 ,2 ]
机构
[1] Max Planck Inst Mol Physiol, Abt Chem Biol, D-44227 Dortmund, Germany
[2] Univ Dortmund, Fachbereich 3, D-44227 Dortmund, Germany
关键词
D O I
10.1039/b717635j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient reagent-controlled methodology for generating highly substituted diverse scaffolds from a common substrate has been developed; thus, treatment of a common precursor with different desilylating reagents, such as ammonium fluoride, caesium fluoride and PPTS, triggers different domino reaction sequences, yielding highly substituted pyridines, phenols and benzopyrans, respectively; the substituent patterns of these scaffolds provide further opportunities for library development.
引用
收藏
页码:1211 / 1213
页数:3
相关论文
共 41 条
[1]   Exploring new chemical space by stereocontrolled diversity-oriented synthesis [J].
Arya, P ;
Joseph, R ;
Gan, ZH ;
Rakic, B .
CHEMISTRY & BIOLOGY, 2005, 12 (02) :163-180
[2]   Asymmetric solid-phase synthesis of 6,6-spiroketals [J].
Baran, O ;
Sommer, S ;
Waldmann, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (24) :3195-3199
[3]   Natural product-guided synthesis of a spiroacetal collection reveals modulators of tubulin cytoskeleton integrity [J].
Barun, O ;
Kumar, K ;
Sommer, S ;
Langerak, A ;
Mayer, TU ;
Müller, O ;
Waldmann, H .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (22) :4773-4788
[4]  
Breinbauer R, 2002, ANGEW CHEM INT EDIT, V41, P2879
[5]   Generating diverse skeletons of small molecules combinatorially [J].
Burke, MD ;
Berger, EM ;
Schreiber, SL .
SCIENCE, 2003, 302 (5645) :613-618
[6]   Identification of inhibitors for mycobacterial protein tyrosine phosphatase B (MptpB) by biology-oriented synthesis (BIOS) [J].
Correa, Ivan R., Jr. ;
Noeren-Mueller, Andrea ;
Ambrosi, Horst-Dieter ;
Jakupovic, Sven ;
Saxena, Krishna ;
Schwalbe, Harald ;
Kaiser, Markus ;
Waldmann, Herbert .
CHEMISTRY-AN ASIAN JOURNAL, 2007, 2 (09) :1109-1126
[7]   Development and biological evaluation of acyl protein thioesterase 1 (APT1) inhibitors [J].
Deck, P ;
Pendzialek, D ;
Biel, M ;
Wagner, M ;
Popkirova, B ;
Ludolph, B ;
Kragol, G ;
Kuhlmann, J ;
Giannis, A ;
Waldmann, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (31) :4975-4980
[8]   Stereocomplementary synthesis of a natural product-derived compound collection on a solid phase [J].
Garcia, Ana B. ;
Lessmann, Torben ;
Umarye, Jayant D. ;
Mamane, Victor ;
Sommer, Stefan ;
Waldmann, Herbert .
CHEMICAL COMMUNICATIONS, 2006, (37) :3868-3870
[9]   THE SYNTHESIS OF PYRIDINE-DERIVATIVES FROM 3-FORMYLCHROMONE [J].
HAAS, G ;
STANTON, JL ;
VONSPRECHER, A ;
WENK, P .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1981, 18 (03) :607-612
[10]  
Hinterding K, 1998, ANGEW CHEM INT EDIT, V37, P688, DOI 10.1002/(SICI)1521-3773(19980403)37:6<688::AID-ANIE688>3.0.CO