THE PALLADIUM-MEDIATED CROSS COUPLING OF BROMOTROPOLONES WITH ORGANOSTANNANES OR ARYLBORONIC ACIDS - APPLICATIONS TO THE SYNTHESIS OF NATURAL-PRODUCTS AND NATURAL PRODUCT ANALOGS

被引：48
作者：
BANWELL, MG
CAMERON, JM
COLLIS, MP
CRISP, GT
GABLE, RW
HAMEL, E
LAMBERT, JN
MACKAY, MF
REUM, ME
SCOBLE, JA
机构：
[1] UNIV ADELAIDE,DEPT ORGAN CHEM,ADELAIDE,SA 5001,AUSTRALIA
[2] LA TROBE UNIV,DEPT CHEM,BUNDOORA,VIC 3083,AUSTRALIA
[3] NCI,NCT,DTP,MOLEC PHARMACOL LAB,BETHESDA,MD 20892
来源：
AUSTRALIAN JOURNAL OF CHEMISTRY | 1991年 / 44卷 / 05期
关键词：
D O I：
10.1071/CH9910705
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The bromotropolones (4), (5) and (10) undergo palladium-mediated cross coupling with a wide range of organostannanes to produce alkenyl-, alkyl- and aryl-substituted tropolones. The methodology has been applied to the synthesis of the monoterpenes beta-dolabrin (11), beta-thujaplicin (12), 4-isopropyl-7-methoxytropolone (13) and beta-thujaplicinol (14). Cross coupling of bromotropolones (4), (5) and (10) with various aryltrimethylstannanes or arylboronic acids has permitted the preparation of the bicyclic colchicine analogues (30)-(43) which have been tested for tubulin-binding activity. The X-ray crystal structure of the most active of these systems, compound (38), is reported.
引用
收藏
页码：705 / 728
页数：24
相关论文
共 49 条
[1]   OXIDATION OF VICINAL DIOLS TO ALPHA-DICARBONYL COMPOUNDS BY TRIFLUOROACETIC-ANHYDRIDE ACTIVATED DIMETHYLSULFOXIDE [J].
AMON, CM ;
BANWELL, MG ;
GRAVATT, GL .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (22) :4851-4855
[2]  
ASAO T, 1985, METHODEN ORG CHEM C, V2, P710
[3]   SYNTHESIS, X-RAY CRYSTAL-STRUCTURE, AND ANTIMITOTIC PROPERTIES OF 6-CHLORO-2-METHOXY-5-(2',3',4'-TRIMETHOXYPHENYL)CYCLOHEPTA-2,4,6-TRIEN-1-ONE, A BICYCLIC ANALOG OF COLCHICINE [J].
BANWELL, MG ;
HERBERT, KA ;
BUCKLETON, JR ;
CLARK, GR ;
RICKARD, CEF ;
LIN, CM ;
HAMEL, E .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (21) :4945-4952
[4]   AN EFFICIENT SYNTHESIS OF 5-BROMO-2-HYDROXYCYCLO-HEPTA-2,4,6-TRIEN-1-ONE AND ITS METHYL-ETHER [J].
BANWELL, MG ;
LAMBERT, JN ;
REUM, ME ;
ONRUST, R .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1988, 20 (04) :393-399
[5]   NEW METHODS FOR THE SYNTHESIS OF TROPONOID COMPOUNDS [J].
BANWELL, MG .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1991, 44 (01) :1-36
[6]   THE PALLADIUM-MEDIATED CROSS-COUPLING OF BROMOTROPOLONES WITH ORGANOSTANNANES - APPLICATION TO CONCISE SYNTHESES OF BETA-DOLABRIN, BETA-THUJAPLICIN, 7-METHOXY-4-ISOPROPYLTROPOLONE, AND BETA-THUJAPLICINOL [J].
BANWELL, MG ;
COLLIS, MP ;
CRISP, GT ;
LAMBERT, JN ;
REUM, ME ;
SCOBLE, JA .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (10) :616-617
[7]   A VERSATILE NEW STRATEGY FOR THE SYNTHESIS OF TROPOLONES [J].
BANWELL, MG ;
ONRUST, R .
TETRAHEDRON LETTERS, 1985, 26 (37) :4543-4546
[8]  
BERLIN J, COMMUNICATION
[9]   COLCHICINE AND ITS ANALOGS - RECENT FINDINGS [J].
BROSSI, A ;
YEH, HJC ;
CHRZANOWSKA, M ;
WOLFF, J ;
HAMEL, E ;
LIN, CM ;
QUIN, F ;
SUFFNESS, M ;
SILVERTON, J .
MEDICINAL RESEARCH REVIEWS, 1988, 8 (01) :77-94
[10]  
Capraro H.G., 1984, ALKALOIDS, V23, P1
12345