title: Highly stereoselective radical cyclization of haloacetals controlled by the acetal center.
abstract: A systematic investigation of radical haloacetal cyclizations (Ueno-Stork reaction) where the acetal center is the unique stereogenic element is reported. This highly diastereoselective reaction can be used for the preparation of polysubstituted tetrahydrofurans and gamma-lactones. We report herein the full experimental details of reactions where up to three new chiral centers are created. To demonstrate the potential of this approach, short syntheses of (+)-eldanolide and of tricyclic acetals related to biologically active lignans have been achieved.
authors.affiliation: University of Fribourg, Department of Chemistry Pérolles, Switzerland.
authors.forename: Félix
authors.initials: F
authors.lastname: Villar
authors.forename: Tanja
authors.initials: T
authors.lastname: Kolly-Kovac
authors.forename: Olivier
authors.initials: O
authors.lastname: Equey
authors.forename: Philippe
authors.initials: P
authors.lastname: Renaud