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Publicly Available Published by De Gruyter January 18, 2011

New samarium diiodide-induced cyclizations

Christine Beemelmanns and Hans-Ulrich Reissig

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.


Conference

International Conference on Organic Synthesis (ICOS-18), International Conference on Organic Synthesis, ICOS, Organic Synthesis, 18th, Bergen, Norway, 2010-08-01–2010-08-06


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Online erschienen: 2011-1-18
Erschienen im Druck: 2011-1-18

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