title: Chiral Diselenides in the Total Synthesis of (+)-Samin.
abstract: Chiral selenium compounds are applied to stoichiometric as well as to catalytic reactions in the synthesis of substituted tetrahydrofuran derivatives: The selenium compound 1 was used in catalytic amounts for a rapid access to chiral diselenide 3. The efficient stereoselective addition to alkene 5 yields product 8 with a selenium functionality as a precursor for an intramolecular radical cyclization. In this way a short total synthesis of (+)-samin (11), a naturally occurring furofuran lignan, was achieved.
authors.affiliation: Institut für Organische Chemie der Universität Basel, St. Johanns-Ring 19, CH-4056 Basel, Switzerland.
authors.forename: Thomas
authors.initials: T
authors.lastname: Wirth
authors.forename: Klaus J.
authors.initials: KJ
authors.lastname: Kulicke
authors.forename: Gianfranco
authors.initials: G
authors.lastname: Fragale