
%0 Journal Article
%A Mayer, Guido 
%A Hinze, Claudia 
%A Polborn, Kurt 
%A Steglich, Wolfgang 
%T Unexpected Formation of the Arcyriacyanin System by Condensation of a 3-Bromo-4-(indol-3-yl)maleimide with (2-Nitrophenyl)acetates
%J Australian Journal of Chemistry
%D 2004/07/07
%V 57
%N 7
%P 625-628
%K 
%R https://doi.org/10.1071/CH04043
%U https://www.publish.csiro.au/paper/CH04043 
%X The reaction of an N-protected 3-bromo-4-(indol-3-yl)maleimide with methyl (2-nitrophenyl)acetates in the presence of base affords condensed cycloheptatriene derivatives which can be transformed into arcyriacyanin-type alkaloids. The unusual reaction sequence implies a heptatrienyl&#8211;cycloheptadienyl anion rearrangement followed by a 1,5-sigmatropic shift to yield the thermodynamically more stable cycloheptatriene derivative. 
