title: Flexible Total Synthesis of (±)-Aureothin, a Potent Antiproliferative Agent.
abstract: Amenable to late-stage preparation of analogues, a flexible and convergent total synthesis of (±)-aureothin is presented. The strategy was based on a desymmetrization of α,α'-dimethoxy-γ-pyrone by a process combining 1,4-addition and alkylation of vinylogous enolate to stereoselectively reach the backbone of the target. Palladium-catalyzed cyanation of an elaborated and isomerizable E,Z dienyl motif followed by Pinner cyclization enabled the construction of the tetrahydrofuran motif while a first approach based on a late-stage oxidation was unsuccessful.
authors.affiliation: COBRA-IRCOF, CNRS, Université & INSA de Rouen , Mont Saint Aignan, France.
authors.forename: Matthias
authors.initials: M
authors.lastname: Henrot
authors.affiliation: COBRA-IRCOF, CNRS, Université & INSA de Rouen , Mont Saint Aignan, France.
authors.forename: Alexandre
authors.initials: A
authors.lastname: Jean
authors.affiliation: COBRA-IRCOF, CNRS, Université & INSA de Rouen , Mont Saint Aignan, France.
authors.forename: Philippe A
authors.initials: PA
authors.lastname: Peixoto
authors.affiliation: COBRA-IRCOF, CNRS, Université & INSA de Rouen , Mont Saint Aignan, France.
authors.forename: Jacques
authors.initials: J
authors.lastname: Maddaluno
authors.affiliation: COBRA-IRCOF, CNRS, Université & INSA de Rouen , Mont Saint Aignan, France.
authors.forename: Michaël
authors.initials: M
authors.lastname: De Paolis
mesh_terms: D000478:Alkylation; D000935:Antifungal Agents / Q000138:chemical synthesis*; D002384:Catalysis; D002867:Chromones / Q000138:chemical synthesis*; D061565:Cycloaddition Reaction; D005663:Furans / Q000138:chemical synthesis; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D010165:Palladium; D013237:Stereoisomerism
chemical_list: D000935:Antifungal Agents; D002867:Chromones; D005663:Furans; D010165:Palladium; C012198:aureothin