title: Stereoselective Synthesis of Ezetimibe via Cross-Metathesis of Homoallylalcohols and α-Methylidene-β-Lactams.
abstract: Ru-catalyzed cross-metathesis (CM) reaction between β-arylated α-methylidene-β-lactams and terminal olefins was developed. The CM reaction is effectively catalyzed with Hoveyda-Grubbs second-generation catalyst affording corresponding α-alkylidene-β-aryl-β-lactams in good isolated yields (41-83%) with exclusive Z-selectivity. The developed protocol was successfully applied for stereoselective preparation of Ezetimibe, the commercial cholesterol absorption inhibitor.
authors: Department of Organic Chemistry, Faculty of Science and ‡Department of Inorganic Chemistry, Faculty of Science, Charles University in Prague , Hlavova 2030/8, 12843 Praha 2, Czech Republic.
authors: Marek
authors: M
authors: Humpl
authors: Department of Organic Chemistry, Faculty of Science and ‡Department of Inorganic Chemistry, Faculty of Science, Charles University in Prague , Hlavova 2030/8, 12843 Praha 2, Czech Republic.
authors: Jiří
authors: J
authors: Tauchman
authors: Department of Organic Chemistry, Faculty of Science and ‡Department of Inorganic Chemistry, Faculty of Science, Charles University in Prague , Hlavova 2030/8, 12843 Praha 2, Czech Republic.
authors: Nikola
authors: N
authors: Topolovčan
authors: Department of Organic Chemistry, Faculty of Science and ‡Department of Inorganic Chemistry, Faculty of Science, Charles University in Prague , Hlavova 2030/8, 12843 Praha 2, Czech Republic.
authors: Jan
authors: J
authors: Kretschmer
authors: Department of Organic Chemistry, Faculty of Science and ‡Department of Inorganic Chemistry, Faculty of Science, Charles University in Prague , Hlavova 2030/8, 12843 Praha 2, Czech Republic.
authors: Filip
authors: F
authors: Hessler
authors: Department of Organic Chemistry, Faculty of Science and ‡Department of Inorganic Chemistry, Faculty of Science, Charles University in Prague , Hlavova 2030/8, 12843 Praha 2, Czech Republic.
authors: Ivana
authors: I
authors: Císařová
authors: Department of Organic Chemistry, Faculty of Science and ‡Department of Inorganic Chemistry, Faculty of Science, Charles University in Prague , Hlavova 2030/8, 12843 Praha 2, Czech Republic.
authors: Martin
authors: M
authors: Kotora
authors: Department of Organic Chemistry, Faculty of Science and ‡Department of Inorganic Chemistry, Faculty of Science, Charles University in Prague , Hlavova 2030/8, 12843 Praha 2, Czech Republic.
authors: Jan
authors: J
authors: Veselý
mesh_terms: D000924:Anticholesteremic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D000069438:Ezetimibe / Q000138:chemical synthesis* / Q000737:chemistry; D020005:Propanols / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry; D013057:Spectrum Analysis / Q000379:methods; D013237:Stereoisomerism; D047090:beta-Lactams / Q000737:chemistry*
chemical_list: D000924:Anticholesteremic Agents; D020005:Propanols; D047090:beta-Lactams; C006463:allyl alcohol; D012428:Ruthenium; D000069438:Ezetimibe