Enantioselective Synthesis of Tetrahydrocarbazoles through a Michael Addition/Ciamician-Plancher Rearrangement Sequence: Asymmetric Synthesis of a Potent Constrained Analogue of MS-245

Awakening an ancient rearrangement: A one‐pot sequential Friedel–Crafts‐type Michael addition/Ag+‐mediated Ciamician–Plancher rearrangement reaction on C2,C3‐nonsubstituted indoles can be used for accessing enantiomerically enriched pharmaceutically relevant 1,2,3,4‐tetrahydrocarbazoles. The methodo...

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Bibliographic Details
Published in:Chemistry : a European journal 2012-10, Vol.18 (42), p.13250-13254
Main Authors: Loh, Charles C. J., Raabe, Gerhard, Enders, Dieter
Format: Article
Language:English
Subjects:
Carbazoles - chemical synthesis
Carbazoles - chemistry
Catalysis
Chemistry
Ciamician-Plancher rearrangement
Crystallography, X-Ray
Indoles - chemistry
Michael additions
Molecular Conformation
organocatalysis
Receptors, Serotonin - chemistry
Receptors, Serotonin - metabolism
Serotonin Antagonists - chemical synthesis
Serotonin Antagonists - chemistry
Silver - chemistry
Stereoisomerism
tandem reactions
tetrahydrocarbazoles
Tryptamines - chemistry
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Summary:Awakening an ancient rearrangement: A one‐pot sequential Friedel–Crafts‐type Michael addition/Ag+‐mediated Ciamician–Plancher rearrangement reaction on C2,C3‐nonsubstituted indoles can be used for accessing enantiomerically enriched pharmaceutically relevant 1,2,3,4‐tetrahydrocarbazoles. The methodology was applied in an enantioselective total synthesis of a highly potent serotonin 5‐HT6 receptor antagonist (see scheme).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201202908