New Samarium Diiodide Induced Cyclizations

Beemelmanns C, Reissig HU (2011) New Samarium Diiodide Induced Cyclizations Pure Appl. Chem. 83, 507-518.


Samarium diiodide (SmI2) smoothly promotes the cyclizations of suitably substituted carbonyl compounds with styrene subunits leading to benzannulated cyclooctenes. The intramolecular samarium ketyl addition to arene or hetarene moieties enables a new, efficient, and highly stereoselective entry to dearomatized products such as hexahydronaphthalenes, steroid-like tetra- or pentacyclic compounds, or dihydroindole derivatives. The usefulness of the developed SmI2-induced cyclization method was demonstrated by the shortest formal total synthesis of the alkaloid strychnine.


Christine Beemelmanns


doi: 10.1351/PAC-CON-10-09-06