Multicomponent Reaction Discovery: Three-Component Synthesis of Spirooxindoles

被引:119
作者
Liang, Bo
Kalidindi, Srinivas
Porco, John A., Jr.
Stephenson, Corey R. J. [1 ]
机构
[1] Boston Univ, Dept Chem, Boston, MA 02215 USA
关键词
ASYMMETRIC TOTAL-SYNTHESIS; 2H-INDOL-2-ONE RING-SYSTEM; SPIROTRYPROSTATIN-A; OXINDOLES; PRODUCTS; CONCISE; ANALOGS; FACILE; ACID; DNA;
D O I
10.1021/ol902764k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Lewis acid-catalyzed, three-component reaction of isatin and two 1,3-dicarbonyl compounds is reported. Reactions proceed with high efficiency under mild reaction conditions and with good functional group tolerance to afford spirooxindole pyranochromenedione derivatives.
引用
收藏
页码:572 / 575
页数:4
相关论文
共 25 条
[1]  
Alper PB, 1999, ANGEW CHEM INT EDIT, V38, P3186, DOI 10.1002/(SICI)1521-3773(19991102)38:21<3186::AID-ANIE3186>3.0.CO
[2]  
2-E
[3]   A SPECTACULAR EXAMPLE OF THE IMPORTANCE OF ROTATIONAL BARRIERS - THE IONIZATION OF MELDRUMS ACID [J].
ARNETT, EM ;
HARRELSON, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (03) :809-812
[4]   Catalytic asymmetric synthesis of quaternary carbon centers.: Exploratory investigations of intramolecular Heck reactions of (E)-α,β-Unsaturated 2-haloanilides and analogues to form enantioenriched spirocyclic products [J].
Ashimori, A ;
Bachand, B ;
Overman, LE ;
Poon, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (26) :6477-6487
[5]   Discovery of chemical reactions through multidimensional screening [J].
Beeler, Aaron B. ;
Su, Shun ;
Singleton, Chris A. ;
Porco, John A., Jr. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (05) :1413-1419
[6]   Stereoselective Synthesis of Spirocyclic Oxindoles via Prins Cyclizations [J].
Castaldi, M. Paola ;
Troast, Dawn M. ;
Porco, John A., Jr. .
ORGANIC LETTERS, 2009, 11 (15) :3362-3365
[7]   Total synthesis of spirotryprostatin A, leading to the discovery of some biologically promising analogues [J].
Edmondson, S ;
Danishefsky, SJ ;
Sepp-Lorenzino, L ;
Rosen, N .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (10) :2147-2155
[8]   Electrocatalytic multicomponent transformation of cyclic 1,3-diketones, isatins, and malononitrile:: facile and convenient way to functionalized spirocyclic (5,6,7,8-tetrahydro-4H-chromene)-4,3′-oxindole system [J].
Elinson, Michail N. ;
Ilovaisky, Alexey I. ;
Dorofeev, Alexander S. ;
Merkulova, Valentina M. ;
Stepanov, Nikita O. ;
Miloserdov, Fedor M. ;
Ogibin, Yuri N. ;
Nikishin, Gennady I. .
TETRAHEDRON, 2007, 63 (42) :10543-10548
[9]  
England DB, 2007, HETEROCYCLES, V74, P491
[10]   Substitution and cyclization reactions involving the quasi-antiaromatic 2H-indol-2-one ring system [J].
England, Dylan B. ;
Merey, Gokce ;
Padwa, Albert .
ORGANIC LETTERS, 2007, 9 (19) :3805-3807