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Synthesis of the ABCD fragment of gymnocin-B
Institution:1. School of Physics and Physical Engineering, Qufu Normal University, Qufu 273165, China;2. Shandong Collegial Key Laboratory of Biotechnology and Utilization of Biological Resources, College of Life Science, Dezhou University, Dezhou 253023, China;1. United Graduate School of Agricultural Science, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan;2. Division of Instrumental Analysis, Life Science Research Center, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan;3. Faculty of Applied Biological Sciences, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan;1. Université de Monastir, Laboratoire de Synthèse Hétérocyclique, Produits Naturels et Réactivités, Faculté des Sciences de Monastir, Avenue de l’Environnement, 5000 Monastir, Tunisia;2. Université de Lyon, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, UMR CNRS 5246, Laboratoire de Chimie Organique 2-Glycochimie, Bâtiment Curien, 43 boulevard du 11 Novembre 1918, F-69622 Villeurbanne, France
Abstract:A convergent synthesis of the ABCD fragment of gymnocin-B was accomplished. The tetracyclic ether ring system was synthesized by the construction of the BC ring system via the oxiranyl anion alkylation and ring expansion reaction, followed by the formation of the five-membered A-ring via a stereoselective radical cyclization reaction of a neopentyl-type iodide.
Keywords:Marine natural product  Gymnocin-B  Polycyclic ether  Oxiranyl anion
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