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2004
Alkaloids
U 0600
45- 217
Unexpected Formation of the Arcyriacyanin System by Condensation of a 3-Bromo-4-(indol-3-yl)maleimide with (2-Nitrophenyl)acetates. — The condensation of
the indolylmaleimide (I) with the (2-nitrophenyl)acetate (II) in the presence of a base
gives the condensed cycloheptatriene (III). The unusual reaction sequence implies a
heptatrienyl—cycloheptadienyl anion rearrangement followed by a 1,5-sigmatropic
shift. The method can be successfully applied in the synthesis of the methylated form
(IX) of the slime mould alkaloid arcyriacyanin A. — (MAYER, G.; HINZE, C.;
POLBORN, K.; STEGLICH*, W.; Aust. J. Chem. 57 (2004) 7, 625-628; Fachbereich
Chem., Ludwig-Maximilians-Univ., D-81377 Muenchen, Germany; Eng.) —
Kieslich
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