New samarium diiodide-induced cyclizations

✍ Scribed by Beemelmanns, Christine; Reissig, Hans-Ulrich

• Book ID: 111873159
• Publisher: International Union of Pure and Applied Chemistry
• Year: 2011
• Tongue: English
• Weight: 801 KB
• Volume: 83
• Category: Article
• ISSN: 0033-4545
• DOI: 10.1351/pac-con-10-09-06

✦ Synopsis

Samarium diiodide (SmI~2~) 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 SmI~2~-induced cyclization method was demonstrated by the shortest formal total synthesis of the alkaloid strychnine.