New metal-catalyzed carbocyclization reactions for the construction of complex natural products

被引：8

作者：

Evans, P. Andrew ^{[1
]}

Baum, Erich W. ^{[1
]}

Fazal, Aleem N. ^{[1
]}

Lai, Kwong Wah ^{[1
]}

Robinson, John E. ^{[1
]}

Sawyer, James R. ^{[1
]}

机构：

[1] Indiana Univ, Dept Chem, Bloomington, IN 47405 USA

来源：

ARKIVOC | 2006年

关键词：

carbocyclization; diastereoselectivity; enantioselective; metallacycles; polycyclic; rhodium-catalyzed;

D O I：

10.3998/ark.5550190.0007.725

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chemo- and stereoselective aspects of the rhodium-catalyzed [m+n+o] carbocyclization reactions of carbon and heteroatom tethered 1,6-enynes with dienes and alkynes are described. The inter- and intramolecular rhodium-catalyzed [4+2+2] carbocyclization reactions provide a convenient and highly diastereoselective approach to bicyclooctanoids, in which the intramolecular version utilizing a temporary silicon-tether circumvents the issues of poor selectivity and reactivity with substituted dienes. The crossed intermolecular rhodium-catalyzed [2+2+2] carbocyclization reaction provides a convenient approach to bicyclohexadienes, in which the regio- and enantioselective variant addresses the challenges with the regiochemical incorporation of unsymmetrical alkynes.

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页码：338 / 358

页数：21

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