Pd(II)-catalysed aminocarbonylation as a key step in the total synthesis of C-6 homologues of 1-deoxynojirimycin and 1-deoxy-l-idonojirimycin |
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| Institution: | 1. Department of Organic Chemistry, Faculty of Chemical Technology, Slovak University of Technology, Radlinského 9, 812 37 Bratislava, Slovakia;2. Department of Inorganic Chemistry, Faculty of Chemical Technology, Slovak University of Technology, Radlinského 9, 812 37 Bratislava, Slovakia;3. Central NMR Laboratories, Faculty of Chemical Technology, Slovak University of Technology, Radlinského 9, 812 37 Bratislava, Slovakia;1. Department of Applied Molecular Biosciences, Graduate School of Bioagricultural Sciences, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8601, Japan;2. Synthetic Cellular Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan;3. Biotechnology Research Center, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398, Japan;4. Japan Science and Technology Agency, ERATO, Ito Glycotrilogy Project, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan;1. Department of Pharmaceutical Sciences, School of Pharmacy, Bouvé College of Health Sciences, Northeastern University, Boston, Massachusetts, USA;2. Department of Cardiac Biology, Xention Ltd, Cambridge, UK;3. Department of Molecular Pharmacology & Physiology, Morsani College of Medicine, University of South Florida, Tampa, Florida, USA;4. Center for Drug Discovery, Northeastern University, Boston, Massachusetts, USA;5. Department of Chemistry and Chemical Biology, College of Science, Northeastern University, Boston, Massachusetts, USA |
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| Abstract: | The first successful Pd(II)-catalysed aminocarbonylation of the highly substituted benzylaminoalkene 5 allows the direct preparation of fused piperidine lactones 3 and 4, which are subsequently converted to the novel C-6 homologue of 1-deoxynojirimycin 1 and 1-deoxy-l-idonojirimycin 2. The study of the influence of various catalytic conditions on the diastereoselectivity and product distribution of the key aminocarbonylation is presented. |
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