title: Synthesis of the gymnodimine tetrahydrofuran core through a Ueno-Stork radical cyclization.
abstract: A straightforward access to the C10-C20 skeleton of gymnodimine, incorporating a tetrahydrofuran fragment, is described. The elaboration of the THF moiety is based on a stereocontrolled Ueno-Stork cyclization. A Lewis-acid mediated allylation of the resulting acetal at C13 and a Horner-Wadsworth-Emmons olefination on the ketone at C17 complete the synthesis.
authors.affiliation: Université de Bordeaux, Institut des Sciences Moléculaires, UMR-CNRS 5255, Talence, France.
authors.forename: Sylvestre
authors.initials: S
authors.lastname: Toumieux
authors.forename: Redouane
authors.initials: R
authors.lastname: Beniazza
authors.forename: Valérie
authors.initials: V
authors.lastname: Desvergnes
authors.forename: Rómulo
authors.initials: R
authors.lastname: Aráoz
authors.forename: Jordi
authors.initials: J
authors.lastname: Molgó
authors.forename: Yannick
authors.initials: Y
authors.lastname: Landais
mesh_terms: D002384:Catalysis; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry*; D006575:Heterocyclic Compounds, 3-Ring / Q000737:chemistry*; D006844:Hydrocarbons, Cyclic / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D005663:Furans; D006575:Heterocyclic Compounds, 3-Ring; D006844:Hydrocarbons, Cyclic; D007097:Imines; C018674:tetrahydrofuran; C407350:gymnodimine