title: Asymmetric synthesis of vabicaserin via oxidative multicomponent annulation and asymmetric hydrogenation of a 3,4-substituted quinolinium salt.
abstract: An efficient, asymmetric synthesis of the 5-HT2C agonist vabicaserin in four chemical steps and 54% overall yield from commercially available benzodiazepine was achieved. The synthesis was highlighted by a novel oxidative, multicomponent reaction to affect the quinolinium ring assembly in one step followed by an unprecedented asymmetric hydrogenation of a 3,4-substituted quinolinium salt.
authors.affiliation: Pharmaceutical Sciences, Pfizer, Inc. , Eastern Point Road, Groton, Connecticut 06340, United States, and Global Supply, Pfizer, Inc. , 100 U.S. 206, Peapack, New Jersey 07970, United States.
authors.forename: Vladimir
authors.initials: V
authors.lastname: Dragan
authors.forename: J Christopher
authors.initials: JC
authors.lastname: McWilliams
authors.forename: Ross
authors.initials: R
authors.lastname: Miller
authors.forename: Karen
authors.initials: K
authors.lastname: Sutherland
authors.forename: John L
authors.initials: JL
authors.lastname: Dillon
authors.forename: Michael K
authors.initials: MK
authors.lastname: O'Brien
mesh_terms: D002384:Catalysis; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D006865:Hydrogenation; D015394:Molecular Structure; D011806:Quinolinium Compounds / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D006576:Heterocyclic Compounds, 4 or More Rings; D011806:Quinolinium Compounds; C556517:vabicaserin