Application of clay catalysts in organic synthesis. a review
01 Feb 2008-Organic Preparations and Procedures International (Taylor & Francis Group)-Vol. 40, Iss: 1, pp 1-65
TL;DR: In this article, the application of clay catalyssts in ORGANIC SYNTHESIS is discussed. And a review of the application can be found in the Appendix.
About: This article is published in Organic Preparations and Procedures International.The article was published on 2008-02-01. It has received 66 citations till now. The article focuses on the topics: Organic synthesis.
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References
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TL;DR: The preparative-scale, enantioselective, total syntheses of members of the hapalindole, fischerindoles, welwitindolinone and ambiguine families are described, each constructed without the need for protecting groups, making it possible to access other complex molecular architectures without using protecting groups.
Abstract: The field of organic synthesis has made phenomenal advances in the past fifty years, yet chemists still struggle to design synthetic routes that will enable them to obtain sufficient quantities of complex molecules for biological and medical studies. Total synthesis is therefore increasingly focused on preparing natural products in the most efficient manner possible. Here we describe the preparative-scale, enantioselective, total syntheses of members of the hapalindole, fischerindole, welwitindolinone and ambiguine families, each constructed without the need for protecting groups—the use of such groups adds considerably to the cost and complexity of syntheses. As a consequence, molecules that have previously required twenty or more steps to synthesize racemically in milligram amounts can now be obtained as single enantiomers in significant quantities in ten steps or less. Through the extension of the general principles demonstrated here, it should be possible to access other complex molecular architectures without using protecting groups. Total synthesis, which involves the construction of complex organic molecules from simpler starting materials, has made remarkable progress in the past fifty years. Despite this, the demand for new synthetic routes capable of generating large natural products for further biological studies remains high. A team of chemists has now identified the abandonment of the routine use of 'protecting' groups in synthesis as a way of satisfying this demand. Protecting groups are often used to mask reactive parts of a molecule while chemical transformations take place elsewhere in that molecule. The potential of the 'unprotected' approach was demonstrated by the synthesis of several members of a large class of marine alkaloids without using a single protecting group. The procedure yields significant quantities of molecules that previously required 20 or more distinct chemical operations in 10 steps or fewer. Members of the hapalindole, fischerindole, welwitindolinone and ambiguine families were synthesized, each constructed without the use of a single protecting group. As a consequence, molecules that have previously required 20 or more steps to synthesize racemically in milligram amounts can now be procured as single enantiomers in significant quantities in 10 steps or less.
416 citations
337 citations
TL;DR: The first total syntheses of welwitindolinone A and the most complex members of the f Fischerindole family, fischerindoles I and G, are reported.
Abstract: The first total syntheses of welwitindolinone A and the most complex members of the fischerindole family, fischerindoles I and G, are reported. Highlights of these short, protecting-group-free syntheses include the application of the recently developed direct indole−carbonyl coupling, a simple approach for installing the quaternary center with neighboring chlorine atom, a regioselective dehydrogenation/dehydration cascade to access fischerindole I, and a remarkably facile oxidative ring contraction to construct welwitindolinone A. An alternative biogenetic hypothesis, whose accuracy is suggested by the success of the current syntheses, is also put forth for this alkaloid family.
234 citations
TL;DR: This method gives pyrroles with less nucleophilic multicyclic aromatic amines at room temperature using iodine-catalyzed and montmorillonite KSF-clay-induced modified Paal-Knorr methods.
Abstract: Simple synthesis of substituted pyrroles using iodine-catalyzed and montmorillonite KSF-clay-induced modified Paal-Knorr methods has been accomplished with excellent yields. N-Substituted carbazole has also been prepared by following this method. If one of the reactants is a liquid, the reaction proceeds exceedingly well without a solvent. This method gives pyrroles with less nucleophilic multicyclic aromatic amines at room temperature.
203 citations