Synthesis of 16,17-seco-steroids with iminomethyl-2-pyridine and aminomethylene-2-pyridine structures as chiral ligands for copper ions and molecular oxygen activation |
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| Institution: | 1. Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary;2. Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich Schiller University Jena, Lessingstraße 8, D-07743 Jena, Germany;3. Institute of Inorganic and Analytical Chemistry, Friedrich Schiller University Jena, Lessingstraße 8, D-07743 Jena, Germany;1. Department of Food and Biotechnology, Korea University, Sejong 339-700, Republic of Korea;2. Lee Gil Ya Cancer and Diabetes Institute, Gachon University of Medicine and Science, Incheon 406-840, Republic of Korea;3. Center for Food and Bioconvergence, Research Institute of Agriculture and Life Sciences, Seoul National University, Seoul 151-742, Republic of Korea;4. Department of Agricultural Biotechnology, Seoul National University, Seoul 151-742, Republic of Korea;1. Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan;2. Medical Innovation Center, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan;1. PSL University, Chimie ParisTech-CNRS, Institute of Chemistry for Life & Health Sciences, CSB2D Team, 11 rue Pierre et Marie Curie, 75005, Paris, France;2. SEQENS, 2-8 rue de Rouen, ZI de Limay-Porcheville, 78440, Porcheville, France;1. Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan;2. Textile and Polymer Section, Technology Research Institute of Osaka Prefecture, 2-7-1 Ayumino, Izumi, Osaka 594-1157, Japan;1. Institut für Chemie, Universität Rostock, Albert Einstein Str. 3a, 18059 Rostock, Germany;2. Leibniz-Institut für Katalyse an der Universität Rostock e.V., Albert Einstein Str. 29a, 18059 Rostock, Germany;3. Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary;1. Department of Food Science and Nutrition, Fuli Institute of Food Science, Zhejiang Key Laboratory for Agro-Food Processing, Zhejiang R & D Center for Food Technology and Equipment, Zhejiang University, 866 Yuhangtang Road, Hangzhou 310058, China;2. Songjiang Entry-Exit Inspection and Quarantine Bureau, 2001 Rongle Dong Road, Songjiang Area, Shanghai 201613, China;3. Department of Food Science and Technology, The University of Tennessee, 2510 River Drive, Knoxville, TN 37996-4539, USA |
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| Abstract: | Starting from 16-oximino-3-methoxy-estra-1.3.5(10)-trien-17-one, the 16,17-seco-13α-carbaldehyde with a 16-nitrile function and its corresponding carboxylic acid have been synthesized via a Beckmann fragmentation. The corresponding 13α-amine is available by Curtius degradation of the carboxylic acid. Condensation of the carboxaldehyde with 2-(aminomethyl)pyridine and the primary amine with pyridine-2-carboxaldehyde gave the corresponding iminomethyl-2-pyridine and the aminomethylene-2-pyridine compounds. Copper-mediated ligand hydroxylations with molecular oxygen were not successful. Reasons for this are discussed. |
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