Construction of spiro[pyrrolidine-3,3′-oxindoles] -: Recent applications to the synthesis of oxindole alkaloids

被引:1417
作者
Marti, C [1 ]
Carreira, EM [1 ]
机构
[1] ETH, Organ Chem Lab, CH-8093 Zurich, Switzerland
关键词
alkaloids; natural products; total synthesis; spiro compounds;
D O I
10.1002/ejoc.200300050
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The spiro[pyrrolidine-3,3'-oxindole] ring system is found at the core of a number of alkaloids, which possess significant biological activity and are interesting, challenging targets for chemical synthesis. In the present review, we report on the different strategies for the synthesis of the spiro[pyrrolidine-3,3'-oxindole] ring system in the context of recent synthesis of coerulescine, horsfiline, elacomine, salacin, pteropodine, alstonisine, spirotryprostatin A and B, and strychnofoline. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).
引用
收藏
页码:2209 / 2219
页数:11
相关论文
共 123 条
[1]   INTRAMOLECULAR ALKENE ARYLATIONS FOR RAPID ASSEMBLY OF POLYCYCLIC SYSTEMS CONTAINING QUATERNARY CENTERS - A NEW SYNTHESIS OF SPIROOXINDOLES AND OTHER FUSED AND BRIDGED RING-SYSTEMS [J].
ABELMAN, MM ;
OH, T ;
OVERMAN, LE .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (18) :4130-4133
[2]  
ALI E, 1982, HETEROCYCLES, V19, P1367
[3]  
Alper PB, 1999, ANGEW CHEM INT EDIT, V38, P3186, DOI 10.1002/(SICI)1521-3773(19991102)38:21<3186::AID-ANIE3186>3.3.CO
[4]  
2-5
[5]  
ANGENOT L, 1978, Plantes Medicinales et Phytotherapie, V12, P123
[6]   Catalytic asymmetric synthesis of quaternary carbon centers.: Exploratory studies of intramolecular Heck reactions of (Z)-α,β-unsaturated anilides and mechanistic investigations of asymmetric Heck reactions proceeding via neutral intermediates [J].
Ashimori, A ;
Bachand, B ;
Calter, MA ;
Govek, SP ;
Overman, LE ;
Poon, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (26) :6488-6499
[7]   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
[8]   CATALYTIC ASYMMETRIC-SYNTHESIS OF QUARTERNARY CARBON CENTERS - PALLADIUM-CATALYZED FORMATION OF EITHER ENANTIOMER OF SPIROOXINDOLES AND RELATED SPIROCYCLICS USING A SINGLE ENANTIOMER OF A CHIRAL DIPHOSPHINE LIGAND [J].
ASHIMORI, A ;
OVERMAN, LE .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (17) :4571-4572
[9]   5-ENDO-TRIGONAL RING CLOSURES OF UNSATURATED SULFONES [J].
AUVRAY, P ;
KNOCHEL, P ;
NORMANT, JF .
TETRAHEDRON LETTERS, 1985, 26 (37) :4455-4458
[10]   ORGANOALUMINUM COMPOUNDS .31. NICKEL-CATALYZED CONJUGATE ADDITION OF TRIMETHYLALUMINUM TO CYCLOPROPYL KETONES [J].
BAGNELL, L ;
MEISTERS, A ;
MOLE, T .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1975, 28 (04) :821-824