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Enantioselective Synthesis of Tetrahydrocarbazoles through a Michael Addition/Ciamician–Plancher Rearrangement Sequence: Asymmetric Synthesis of a Potent Constrained Analogue of MS‐245
Author(s) -
Loh Charles C. J.,
Raabe Gerhard,
Enders Dieter
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201202908
Subject(s) - enantioselective synthesis , sequence (biology) , stereochemistry , antagonist , scheme (mathematics) , computer science , chemistry , total synthesis , combinatorial chemistry , mathematics , organic chemistry , catalysis , receptor , biochemistry , mathematical analysis
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‐HT 6 receptor antagonist (see scheme).