Suzuki-Miyaura and Stille reactions as key steps in the synthesis of diversely functionalized Amaryllidaceae alkaloid analogs bearing a 5,6,7,8-tetrahydrobenzo(c,e)azocine skeleton.

Appukkuttan P; Dehaen W; Van-der-Eycken E

首页> 外文期刊>Combinatorial chemistry & high throughput screening >Suzuki-Miyaura and Stille reactions as key steps in the synthesis of diversely functionalized Amaryllidaceae alkaloid analogs bearing a 5,6,7,8-tetrahydrobenzo(c,e)azocine skeleton.

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Suzuki-Miyaura and Stille reactions as key steps in the synthesis of diversely functionalized Amaryllidaceae alkaloid analogs bearing a 5,6,7,8-tetrahydrobenzo(c,e)azocine skeleton.

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摘要

Microwave-assisted Suzuki-Miyaura and Stille cross-coupling reactions for the synthesis of highly electron-rich and diversely functionalized biaryl intermediates are presented. Microwave-irradiation has been demonstrated to be a very powerful tool for performing difficult transition metal-catalyzed cross-coupling reactions with unfavorably substituted coupling partners. The key biaryl intermediates were used for the microwave-enhanced construction of the 5,6,7,8-tetrahydrobenzoc,eazocine skeleton of the Apogalanthamine analogs. The success of the strategy is demonstrated by synthesizing a number of hitherto unknown, diversely functionalized, natural product analogs.

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《Combinatorial chemistry & high throughput screening》 |2007年第9期|790-801|共12页
作者
Appukkuttan P; Dehaen W; Van-der-Eycken E;
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作者单位

Department of Chemistry, University of Leuven, Celestijnenlaan 200F, B-3001 Leuven, Belgium.;

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原文格式 PDF
正文语种英语
中图分类化学;
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analogs; Skeletal system; microwave electromagnetic radiation;

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1. ChemInform Abstract: Synthesis of Erythrina and Related Alkaloids. Part 47. General Method for Synthesis of Erythrinan and Homoerythrinan Alkaloids. Part. 1: Synthesis of a Cycloerythrinan as a Key Intermediate to Erythrina Alkaloids by Pummerer‐Type Reaction. [J] . J. TODA, Y. NIIMURA, K. TAKEDAT. SANOY. TSUDA Chem Inform . 1998,第48期

机译：ChemInform Abstract: Synthesis of Erythrina and Related Alkaloids. Part 47. General Method for Synthesis of Erythrinan and Homoerythrinan Alkaloids. Part. 1: Synthesis of a Cycloerythrinan as a Key Intermediate to Erythrina Alkaloids by Pummerer‐Type Reaction.
2. ChemInform Abstract: Solid‐Phase Synthesis of Structurally Diverse 1,4‐Benzodiazepine Derivatives Using the Stille Coupling Reaction. [J] . M. J. PLUNKETT, J. A. ELLMAN Chem Inform . 1995,第49期

机译：ChemInform Abstract: Solid‐Phase Synthesis of Structurally Diverse 1,4‐Benzodiazepine Derivatives Using the Stille Coupling Reaction.
3. ChemInform Abstract: Total Synthesis of Amaryllidaceae Alkaloids Utilizing Sequential Intramolecular Heterocyclic Azadiene Diels—Alder Reactions of an Unsymmetrical 1,2,4,5‐Tetrazine. [J] . Dale L. Boger, Scott E. Wolkenberg Chem Inform . 2001,第19期

机译：ChemInform Abstract: Total Synthesis of Amaryllidaceae Alkaloids Utilizing Sequential Intramolecular Heterocyclic Azadiene Diels—Alder Reactions of an Unsymmetrical 1,2,4,5‐Tetrazine.

Suzuki-Miyaura and Stille reactions as key steps in the synthesis of diversely functionalized Amaryllidaceae alkaloid analogs bearing a 5,6,7,8-tetrahydrobenzo(c,e)azocine skeleton.

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