title: Direct synthesis of stereodefined and functionalized dienes as valuable building blocks.
abstract: We have reported a direct and stereoselective synthesis of functionalized dienoic carboxylates from the simple bicyclic lactone 1. The use of oxygen- or nitrogen-based nucleophiles in a domino allylic alkylation/4π-electrocyclic ring opening affords reliable access to dienes with interesting functionalities. Alternatively, halide substitution offers synthesis of other classes of functionalized dienoic acids. Herein, we demonstrate the utility of such dienoic products as key building blocks in various transformations as well as natural product synthesis.
authors.affiliation: University of Vienna Institute of Organic Chemistry Währinger Straße 38 A-1090 Vienna, Austria. nuno.maulide@univie.ac.at.
authors.forename: Nuno
authors.initials: N
authors.lastname: Maulide
authors.affiliation: University of Vienna Institute of Organic Chemistry Währinger Straße 38 A-1090 Vienna, Austria.
authors.forename: Caroline
authors.initials: C
authors.lastname: Souris
authors.affiliation: University of Vienna Institute of Organic Chemistry Währinger Straße 38 A-1090 Vienna, Austria.
authors.forename: Frédéric
authors.initials: F
authors.lastname: Frébault
authors.affiliation: University of Vienna Institute of Organic Chemistry Währinger Straße 38 A-1090 Vienna, Austria.
authors.forename: Marco
authors.initials: M
authors.lastname: Luparia
authors.affiliation: University of Vienna Institute of Organic Chemistry Währinger Straße 38 A-1090 Vienna, Austria.
authors.forename: Davide
authors.initials: D
authors.lastname: Audisio
mesh_terms: D000478:Alkylation; D001688:Biological Products / Q000138:chemical synthesis*; D002264:Carboxylic Acids / Q000138:chemical synthesis*; D006219:Halogens / Q000737:chemistry; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D011090:Polyenes / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D002264:Carboxylic Acids; D006219:Halogens; D007783:Lactones; D011090:Polyenes