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A FeCl3-promoted highly atropodiastereoselective cascade reaction: synthetic utility of radical cations in indolostilbene construction |
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| Authors: | Kartini Ahmad Mat Ropi Mukhtar Jean-Frederic Faizal Weber Saraswati S Velu Hiroshi Morita A Hamid A Hadi |
| Institution: | a Department of Chemistry, Faculty of Science and Technology, University Pendidikan Sultan Idris, 35900 Tanjong Malim, Perak, Malaysia b Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia c Department of Biotechnology, Faculty of Science, International Islamic University, Jalan Gombak, 53100 Kuala Lumpur, Malaysia d iKUS, Faculty of Pharmacy, University Teknologi MARA, 40450 Shah Alam, Selangor D.E., Malaysia e Tokyo University of Pharmaceutical and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan f Faculty of Pharmaceutical Sciences, Hoshi University, Shinagawa-ku, Tokyo 142-8501, Japan g Environmental and Bioprocess Technology Centre, SIRIM Berhad, 40000 Shah Alam, Selangor, Malaysia |
| Abstract: | The FeCl3-promoted oxidative cyclization/coupling of acetamidostilbenes possessing 3-methoxy, 4-methoxy and 3,5-methoxy substitutions (21), (22) and (23) is described. Only 3,5-substitution gave rise to novel indolostilbenes, each possessing two stereogenic axes (axially chiral but racemic dimers (39) and (40)). The 4-methoxy substituted acetamidostilbenes, by contrast, yielded the bisindoline dimer (36). |
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