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A tandem highly stereoselective FeCl3-promoted synthesis of a bisindoline: synthetic utility of radical cations in heterocyclic construction |
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| Authors: | Noel F Thomas Saraswati S Velu KC Lee A Hamid A Hadi David Rondeau Khalijah Awang |
| Institution: | a Department of Chemistry, Faculty of Science, University Malaya, 59100 Kuala Lumpur, Malaysia b iKUS, Faculty of Pharmacy, Universiti Teknologi MARA, 40450 Shah Alam, Selangor D.E., Malaysia c Department of Pharmacy, Faculty of Allied Health Sciences, Universiti Kebangsaan Malaysia, 50300 Kuala Lumpur, Malaysia d Faculté des Sciences, Université d'Angers, 2, Boulevard Lavoisier, 49045 Angers, France e Department of Biotechnology, Faculty of Science, International Islamic University, Jalan Gombak, 53100 Kuala Lumpur, Malaysia |
| Abstract: | A conceptually distinctive stereoselective construction of the novel dimer, N-N′-acetyl-7,7′-bis-(3,4-dimethoxy-phenyl)-7,8,7′,8′-tetrahydro-N′H-8,8′]biindolyl-N-yl]-ethanone 25 (bisindoline) is described below. These structures, which include 7-(3,4-dimethoxyphenyl)-indoline 24 (veratryl indoline), were obtained by the tactical combination of palladium-catalysed coupling which produced 10-acetamido-3,4-dimethoxystilbene 9, followed by FeCl3 induced oxidative cyclization/dimerization. All new structures were fully characterized by 1- and 2D NMR spectroscopy, (proton, carbon-13, COSY, HMBC, HMQC) and mass spectrometry. Configurational assignments were further supported by semi-empirical AM1 calculations. Mechanistic interpretations, consistent with our results, are discussed. |
| Keywords: | Ferric chloride Radical cation Bisindole Stereospecific Stilbene |
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