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

Loh Charles C. J. | Zendy; Raabe Gerhard | Zendy; Enders Dieter | Zendy

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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).

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