title: Total synthesis of seco-plakortolide E and (-)-ent-plakortolide I: absolute configurational revision of natural plakortolide I.
abstract: A first total synthesis of (-)-ent-plakortolide I and seco-plakortolide E was accomplished from (S)-2-methylglycidol. The relevant key reactions involve a diastereoselective Mukaiyama aldol reaction, a regioselective hydroperoxysilylation, and elaboration of the 1,2-dioxane ring by intramolecular Michael addition of a hydroperoxide group to a butenolide. This synthesis allowed the revision of the absolute configuration of plakortolide I and structural revision of plakortolide E.
authors.affiliation: Université Lyon 1, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), UMS 5246 CNRS, équipe SURCOOF, bât Raulin, 43 bd du 11 Novembre 1918, Villeurbanne Cedex, France.
authors.forename: Bogdan
authors.initials: B
authors.lastname: Barnych
authors.forename: Jean-Michel
authors.initials: JM
authors.lastname: Vatèle
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D001688:Biological Products / Q000138:chemical synthesis*; D002384:Catalysis; D004146:Dioxanes / Q000138:chemical synthesis*; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis*; D008968:Molecular Conformation; D010545:Peroxides / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D004146:Dioxanes; D006574:Heterocyclic Compounds, 2-Ring; D010545:Peroxides; C093753:plakortolide E; C478290:plakortolide I; D015107:4-Butyrolactone