title: Catalytic asymmetric total syntheses of quinine and quinidine.
abstract: The catalytic, asymmetric syntheses of quinine and quinidine were achieved in 16 steps. The recently developed salen(Al)-catalyzed enantioselective Michael addition of methyl cyanoacetate served to set the crucial C4 stereocenter in 92% ee, and a late-stage asymmetric dihydroxylation was used to differentiate the common intermediate and access the two desired diastereomeric products with high selectivity.
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
authors.forename: Izzat T
authors.initials: IT
authors.lastname: Raheem
authors.forename: Steven N
authors.initials: SN
authors.lastname: Goodman
authors.forename: Eric N
authors.initials: EN
authors.lastname: Jacobsen
mesh_terms: D002384:Catalysis; D011802:Quinidine / Q000138:chemical synthesis*; D011803:Quinine / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D011803:Quinine; D011802:Quinidine