title: Ruthenium-SYNPHOS-catalyzed asymmetric hydrogenations: an entry to highly stereoselective synthesis of the C15-C30 subunit of dolabelide A.
abstract: An efficient construction of the C15-C30 segment of the cytotoxic macrolide dolabelide A is described. The synthesis relies on ruthenium-SYNPHOS-mediated asymmetric hydrogenation reactions of beta-keto esters to generate the C19, C21, and C27 hydroxyl-bearing stereocenters with very high levels of enantio- and diastereoselectivity.
authors.affiliation: Laboratoire de Synthèse Sélective Organique et Produits Naturels UMR 7573 CNRS, ENSCP, 11 rue Pierre et Marie Curie, 75231 Paris Cedex 01, France.
authors.forename: Christophe
authors.initials: C
authors.lastname: Roche
authors.forename: Nicolas
authors.initials: N
authors.lastname: Desroy
authors.forename: Mansour
authors.initials: M
authors.lastname: Haddad
authors.forename: Phannarath
authors.initials: P
authors.lastname: Phansavath
authors.forename: Jean-Pierre
authors.initials: JP
authors.lastname: Genet
mesh_terms: D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry; D006865:Hydrogenation; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis*; D009942:Organometallic Compounds / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D004952:Esters; D007659:Ketones; D018942:Macrolides; D009942:Organometallic Compounds; C481199:dolabelide A; D012428:Ruthenium