Stereocontrolled total synthesis of (+)-vinblastine

被引:203
作者
Yokoshima, S [1 ]
Ueda, T [1 ]
Kobayashi, S [1 ]
Sato, A [1 ]
Kuboyama, T [1 ]
Tokuyama, H [1 ]
Fukuyama, T [1 ]
机构
[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
关键词
D O I
10.1021/ja0177049
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A stereocontrolled total synthesis of (+)-vinblastine was accomplished, featuring preparations of the two indole units by means of a novel indole synthesis via radical cyclization of thioanilide, and a stereoselective coupling of these units. Copyright © 2002 American Chemical Society.
引用
收藏
页码:2137 / 2139
页数:3
相关论文
共 25 条
[1]  
BROSSI A, 1990, ALKALOIDS, V37, P133
[2]   ENANTIOSELECTIVE MICHAEL REACTIONS - DIASTEREOSELECTIVE REACTIONS OF CHLOROTITANIUM ENOLATES OF CHIRAL N-ACYLOXAZOLIDINONES WITH REPRESENTATIVE ELECTROPHILIC OLEFINS [J].
EVANS, DA ;
BILODEAU, MT ;
SOMERS, TC ;
CLARDY, J ;
CHERRY, D ;
KATO, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) :5750-5752
[3]   TOTAL SYNTHESIS OF (+)-CALYCULIN-A [J].
EVANS, DA ;
GAGE, JR ;
LEIGHTON, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (24) :9434-9453
[4]   INDOLE-2,3-QUINODIMETHANES - A NEW STRATEGY FOR THE SYNTHESIS OF TETRACYCLIC SYSTEMS OF INDOLE ALKALOIDS [J].
EXON, C ;
GALLAGHER, T ;
MAGNUS, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (14) :4739-4749
[5]  
FARRAND R, 1990, ORG SYNTH COLL, V7, P302
[6]  
Fujiwara A, 2000, SYNLETT, P1667
[7]   2,4-dinitrobenzenesulfonamides: A simple and practical method for the preparation of a variety of secondary amines and diamines. [J].
Fukuyama, T ;
Cheung, M ;
Jow, CK ;
Hidai, Y ;
Kan, T .
TETRAHEDRON LETTERS, 1997, 38 (33) :5831-5834
[8]   2-NITROBENZENESULFONAMIDES AND 4-NITROBENZENESULFONAMIDES - EXCEPTIONALLY VERSATILE MEANS FOR PREPARATION OF SECONDARY-AMINES AND PROTECTION OF AMINES [J].
FUKUYAMA, T ;
JOW, CK ;
CHEUNG, M .
TETRAHEDRON LETTERS, 1995, 36 (36) :6373-6374
[9]   REISSERT COMPOUNDS . REACTION OF SOME THIOCARBONYL CHLORIDES WITH QUINOLINE ISOQUINOLICE AND PYRIDINE [J].
HULL, R .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (14) :1777-&
[10]   Highly versatile synthesis of nitrogen-containing compounds by means of nitrobenzenesulfonamides [J].
Kan, T ;
Fukuyama, T .
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2001, 59 (08) :779-789