title: A practical synthesis for the core structure of a family of selective prostaglandin D2 receptor antagonists.
abstract: A convergent synthesis was developed for the production of the core structure of prostaglandin D(2) receptor antagonists for the treatment of allergic rhinitis. The key steps in this synthesis were a highly diastereoselective alkylation of (+)-nopinone, a chemo- and stereoselective reduction of an oxime to an amine, and a well-controlled reduction of an aminoalkyne to a (Z)-olefin.
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: Dongwei
authors.initials: D
authors.lastname: Cai
authors.forename: Jason J
authors.initials: JJ
authors.lastname: Kowal
authors.forename: Sandra
authors.initials: S
authors.lastname: Lee
authors.forename: Robert D
authors.initials: RD
authors.lastname: Larsen
authors.forename: Paul J
authors.initials: PJ
authors.lastname: Reider
mesh_terms: D000478:Alkylation; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D003516:Cycloparaffins / Q000138:chemical synthesis; D019906:Nuclear Magnetic Resonance, Biomolecular; D010084:Oxidation-Reduction; D011971:Receptors, Immunologic; D011982:Receptors, Prostaglandin / Q000037:antagonists & inhibitors*; D012221:Rhinitis, Allergic, Perennial / Q000188:drug therapy*; D013237:Stereoisomerism; D013696:Temperature
chemical_list: D001952:Bridged-Ring Compounds; D003516:Cycloparaffins; D011971:Receptors, Immunologic; D011982:Receptors, Prostaglandin; C476481:nopinone; C036293:prostaglandin D2 receptor