G. Mayer, C. Hinze, K. Polborn
Jul 19, 2004
Citations
0
Influential Citations
5
Citations
Journal
Australian Journal of Chemistry
Abstract
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–cycloheptadienyl anion rearrangement followed by a 1,5-sigmatropic shift to yield the thermodynamically more stable cycloheptatriene derivative.