Chiral Diselenides in the Total Synthesis of (+)-Samin.
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.
Wirth
Thomas
T
Institut für Organische Chemie der Universität Basel, St. Johanns-Ring 19, CH-4056 Basel, Switzerland.
Kulicke
Klaus J.
KJ
Fragale
Gianfranco
G