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
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