Abstract
[reaction: see text] Starting from tryptamine 4 and isatin 5, a biomimetic approach to the pentacyclic substructure 1 of perophoramidine and communesin was developed. The key steps were to create a stable three/six bicyclic system 2 on the 2,3-double bond of an indole derivative 3 by an intramolecular cyclopropanation, followed by ring opening of the resulting cyclopropane ring with the in situ generated amine group of an aniline.
Publication types
-
Research Support, Non-U.S. Gov't
MeSH terms
-
Cyclopropanes / chemistry
-
Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
-
Hydrocarbons, Halogenated / chemical synthesis*
-
Isatin / blood
-
Isatin / chemistry
-
Molecular Mimicry
-
Molecular Structure
-
Tryptamines / chemistry
Substances
-
Cyclopropanes
-
Heterocyclic Compounds, 4 or More Rings
-
Hydrocarbons, Halogenated
-
Tryptamines
-
communesin B
-
perophoramidine
-
tryptamine
-
Isatin