Abstract
An asymmetric synthesis was developed for the production of a prostaglandin D(2) receptor antagonist for the treatment of allergic rhinitis. The stereogenic center was set using asymmetric allylic alkylation chemistry, and the core of the structure was constructed via Pd-catalyzed N-cyclization/Heck methodology. The synthesis relies on a late stage indoline oxidation which does not racemize the product.
MeSH terms
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Combinatorial Chemistry Techniques*
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Crystallography, X-Ray
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Cyclization
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Indoles / chemical synthesis*
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Indoles / pharmacology
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Molecular Conformation
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Molecular Structure
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Organometallic Compounds / chemical synthesis*
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Organometallic Compounds / pharmacology
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Oxidation-Reduction
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Palladium / chemistry*
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Receptors, Immunologic / antagonists & inhibitors*
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Receptors, Prostaglandin / antagonists & inhibitors*
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Rhinitis, Allergic, Perennial / drug therapy*
Substances
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Indoles
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Organometallic Compounds
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Receptors, Immunologic
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Receptors, Prostaglandin
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Palladium
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prostaglandin D2 receptor