
%0 Journal Article
%A Banwell, MG 
%A Cameron, JM 
%A Collis, MP 
%A Crisp, GT 
%A Gable, RW 
%A Hamel, E 
%A Lambert, JN 
%A Mackay, MF 
%A Reum, ME 
%A Scoble, JA 
%T The Palladium-Mediated Cross Coupling of Bromotropolones With Organostannanes or Arylboronic Acids: Applications to the Synthesis of Natural Products and Natural Product Analogs
%J Australian Journal of Chemistry
%D 1991/05/01
%V 44
%N 5
%P 705-728
%K 
%R https://doi.org/10.1071/CH9910705
%U https://www.publish.csiro.au/paper/CH9910705 
%X 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 &#946;- dolabrin (11),&#946;- thujaplicin (12), 4-isopropyl-7-methoxytropolone (13) and &#946;- 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. 
