Diastereoselective pot-and atom-economical synthesis of densely-substituted polycyclic 1,2- and 1,2,3-fused indole scaffolds |
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| Institution: | 1. Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-8657, Japan;2. Frontier Research Center for Advanced Material and Life Science, Faculty of Advanced Life Science, Hokkaido University, Kita 21 Nishi 11, Kita-ku, Sapporo 001-0021, Japan;1. College of Chemistry and Chemical Engineering, Xinxiang University, Xinxiang 453000, PR China;2. Medical College, Xinxiang University, Xinxiang 453000, PR China;1. Department of Chemical Engineering, Inner Mongolia University of Technology, 010051 Huhhot, China;2. School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, 430074 Wuhan, China;1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation;2. N. K. Kol’tsov Institute of Developmental Biology, Russian Academy of Sciences, 119334 Moscow, Russian Federation;1. Key Laboratory of Radiopharmaceuticals, Ministry of Education, College of Chemistry, Beijing Normal University, Beijing 100875, China |
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| Abstract: | A simple, efficient, one-pot sequential process for the preparation of a family of 8,9-dihydropyrido1,2–a]indol-6(7H)-one scaffolds in acceptable yields has been established under mild conditions. The Michael-hemiaminalization-oxidation reaction proceeds between methyl 2-(3-formyl-1H-indol-2-yl) acetate and trans-β-aryl/alkyl-substituted acroleins using pyrrolidine-BzOH as an efficient organocatalyst, followed by oxidation of in situ generated of C,N-fused hemiaminal adducts in the presence of PDC at room temperature. Excitingly, organobase-catalyzed highly diastereoselective (up to ≤9:1 dr) construction of a series of pharmacologically attractive 1,2,3-fused tetracyclic indole scaffolds with five contiguous chiral centers including an all-carbon stereogenic center has been realized through our developed method. Moreover, pyrrolidine-BzOH and PTSA as combined catalytic systems promote the uninterrupted sequential Michael-cyclization reaction, followed by N-alkylation reaction with carbazole to produce interesting class of 6-(9H-carbazol-9-yl)-6,7,8,9-tetrahydropyrido1,2–a]indole derivatives in a diastereoselective manner. |
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| Keywords: | Organocatalysts Atom-economical Polycyclic-fused-indoles Diastereoselective |
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