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

页码：507 / 518

页数：12

共 45 条

[1] A new, efficient and stereoselective synthesis of tricyclic and tetracyclic compounds by samarium diiodide induced cyclisations of naphthyl-substituted arylketones -: An easy access to steroid-like skeletons [J].

Aulenta, Francesca ;

Berndt, Mathias ;

Bruedgam, Irene ;

Hartl, Hans ;

Soergel, Sebastian ;

Reissig, Hans-Ulrich .

CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (21) :6047-6062

[2] Nitrogen-containing tricyclic and tetracyclic compounds by stereoselective samarium diiodide promoted cyclizations of quinolyl-substituted ketones -: A new access to azasteroids [J].

Aulenta, Francesca ;

Wefelscheid, Ulrike K. ;

Bruedgam, Irene ;

Reissig, Hans-Ulrich .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (13) :2325-2335

[3]

Beemelmanns C., 2010, ANGEW CHEM, V122, P8195

[4]

BEEMELMANNS C, 2010, CHEM SOC REV, DOI DOI 10.1039/COCS00116C

[5] A Short Formal Total Synthesis of Strychnine with a Samarium Diiodide Induced Cascade Reaction as the Key Step [J].

Beemelmanns, Christine ;

Reissig, Hans-Ulrich .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (43) :8021-8025

[6] Highly Diastereoselective Samarium Diiodide Induced Ketyl Cyclisations of Indole and Pyrrole Derivatives - Scope and Limitations [J].

Beemelmanns, Christine ;

Blot, Virginie ;

Gross, Steffen ;

Lentz, Dieter ;

Reissig, Hans-Ulrich .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (14) :2716-2732

[7] Highly diastereoselective samarium diiodide induced cyclizations of new 3-substituted indole derivatives [J].

Beemelmanns, Christine ;

Reissig, Hans-Ulrich .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (21) :4475-4480

[8] Stereoselective formation of tri- and tetracycles by samarium diiodide-induced cyclizations of naphthyl-substituted ketones [J].

Berndt, M ;

Hlobilová, I ;

Reissig, HU .

ORGANIC LETTERS, 2004, 6 (06) :957-960

[9] New samarium diiodide-induced ketyl couplings -: From analogous reactions to serendipitously discovered processes [J].

Berndt, M ;

Gross, S ;

Hölemann, A ;

Reissig, HU .

SYNLETT, 2004, (03) :422-438

[10]

Berndt M, 2001, SYNLETT, P1290

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