New samarium diiodide-induced cyclizations

Christine Beemelmanns; Hans-Ulrich Reissig

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

Publicly Available Published by De Gruyter January 18, 2011

New samarium diiodide-induced cyclizations

Christine Beemelmanns and Hans-Ulrich Reissig

From the journal Pure and Applied Chemistry

https://doi.org/10.1351/PAC-CON-10-09-06

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.

Keywords: alkenes; alkynes; arenes; cyclooctene derivatives; dearomatization; hetarenes; hexahydronaphthalenes; indoles; ketyls; natural products; samarium diiodide; steroid-like compounds; 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

New samarium diiodide-induced cyclizations

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