New samarium diiodide-induced cyclizations*

نویسندگان

  • Christine Beemelmanns
  • Hans-Ulrich Reissig
چکیده

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 tetraor 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.

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تاریخ انتشار 2011