Abstract
A concise, enantioselective synthesis of the potent dual orexin inhibitor suvorexant (1) is reported. Key features of the synthesis include a mild copper-catalyzed amination, a highly chemoselective conjugate addition, and a tandem enantioselective transamination/seven-membered ring annulation. The synthesis requires inexpensive starting materials and only four linear steps for completion.
MeSH terms
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Azepines / chemical synthesis*
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Azepines / chemistry
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Azepines / pharmacology
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Molecular Structure
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Orexin Receptors
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Receptors, G-Protein-Coupled / antagonists & inhibitors
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Receptors, Neuropeptide / antagonists & inhibitors
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Stereoisomerism
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Structure-Activity Relationship
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Triazoles / chemical synthesis*
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Triazoles / chemistry
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Triazoles / pharmacology
Substances
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Azepines
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Orexin Receptors
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Receptors, G-Protein-Coupled
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Receptors, Neuropeptide
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Triazoles
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suvorexant