Abstract
IRONic electrophilic indoles! The C3-regioselective hydroarylation of N-acetyl indoles with aromatic nucleophiles mediated by FeCl(3) features a rare example of the electrophilic reactivity of the indole core in a Friedel-Crafts reaction. This indole umpolung allows us straightforward access to the tetracyclic benzofuroindoline motif found in the natural product diazonamide A, which is a potent antitumor agent.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Publication types
-
Research Support, Non-U.S. Gov't
MeSH terms
-
Antineoplastic Agents / chemical synthesis*
-
Antineoplastic Agents / chemistry
-
Catalysis
-
Chlorides / chemistry*
-
Ferric Compounds / chemistry*
-
Heterocyclic Compounds, 4 or More Rings / chemical synthesis
-
Heterocyclic Compounds, 4 or More Rings / chemistry
-
Indoles / chemical synthesis
-
Indoles / chemistry*
-
Oxazoles / chemical synthesis
-
Oxazoles / chemistry
-
Stereoisomerism
Substances
-
Antineoplastic Agents
-
Chlorides
-
Ferric Compounds
-
Heterocyclic Compounds, 4 or More Rings
-
Indoles
-
Oxazoles
-
diazonamide A
-
indoline
-
indole
-
ferric chloride