title: Asymmetric total synthesis of (-)-callystatin A employing the SAMP/RAMP hydrazone alkylation methodology.
abstract: [structure: see text] The asymmetric total synthesis of (-)-callystatin A has been achieved. The key steps generating the stereogenic centers rely on the asymmetric alpha-alkylation of aldehydes or ketones exploiting the SAMP/RAMP hydrazone alkylation methodology, as well as an enzymatic enantioselective reduction of a 3,5-dioxocarboxylate. For the construction of the alkene moieties, highly selective Wittig or Horner-Wadsworth-Emmons reactions were employed.
authors.affiliation: Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor Pirlet-Strasse 1, 52074 Aachen, Germany.
authors.forename: Jose L
authors.initials: JL
authors.lastname: Vicario
authors.forename: Andreas
authors.initials: A
authors.lastname: Job
authors.forename: Michael
authors.initials: M
authors.lastname: Wolberg
authors.forename: Michael
authors.initials: M
authors.lastname: Müller
authors.forename: Dieter
authors.initials: D
authors.lastname: Enders
mesh_terms: D000478:Alkylation; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis*; D006835:Hydrazones / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D005231:Fatty Acids, Unsaturated; D006835:Hydrazones; C421091:callystatin A