New samarium diiodide-induced cyclizations

被引：25
作者：
Beemelmanns, Christine [1 ]
Reissig, Hans-Ulrich [1 ]
机构：
[1] Free Univ Berlin, Inst Chem & Biochem, D-14195 Berlin, Germany
来源：
PURE AND APPLIED CHEMISTRY | 2011年 / 83卷 / 03期
关键词：
alkenes; alkynes; arenes; cyclooctene derivatives; dearomatization; hetarenes; hexahydronaphthalenes; indoles; ketyls; natural products; samarium diiodide; steroid-like compounds; strychnine; DIASTEREOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; 6-TRIG CYCLIZATIONS; DERIVATIVES; INDOLE; SPIROCYCLIZATION; ARYLKETONES; EFFICIENT;
D O I：
10.1351/PAC-CON-10-09-06
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
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.
引用
收藏
页码：507 / 518
页数：12
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