title: Asymmetric synthesis of a prostaglandin D2 receptor antagonist.
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.
authors.affiliation: Department of Process Research, Merck Research Laboratories, P.O. Box 2000, RY800-B267, Rahway, New Jersey 07065-0900, USA. kevin_campos@merck.com
authors.forename: Kevin R
authors.initials: KR
authors.lastname: Campos
authors.forename: Michel
authors.initials: M
authors.lastname: Journet
authors.forename: Sandra
authors.initials: S
authors.lastname: Lee
authors.forename: Edward J J
authors.initials: EJ
authors.lastname: Grabowski
authors.forename: Richard D
authors.initials: RD
authors.lastname: Tillyer
mesh_terms: D020650:Combinatorial Chemistry Techniques; D018360:Crystallography, X-Ray; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000494:pharmacology; D008968:Molecular Conformation; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D011971:Receptors, Immunologic / Q000037:antagonists & inhibitors*; D011982:Receptors, Prostaglandin / Q000037:antagonists & inhibitors*; D012221:Rhinitis, Allergic, Perennial / Q000188:drug therapy*
chemical_list: D007211:Indoles; D009942:Organometallic Compounds; D011971:Receptors, Immunologic; D011982:Receptors, Prostaglandin; D010165:Palladium; C036293:prostaglandin D2 receptor