
TY  - JOUR
A1  - Mayer, Guido 
A1  - Hinze, Claudia 
A1  - Polborn, Kurt 
A1  - Steglich, Wolfgang 
T1  - Unexpected Formation of the Arcyriacyanin System by Condensation of a 3-Bromo-4-(indol-3-yl)maleimide with (2-Nitrophenyl)acetates
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 2004
VL  - 57
IS  - 7
SP  - 625
EP  - 628
KW  - 
UR  - https://doi.org/10.1071/CH04043 
N2  - 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. 
ER  -

