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Formal total synthesis of stigmatellin A
Affiliation:1. Key Laboratory of Traffic Safety on Track (Central South University), Ministry of Education, School of Traffic and Transportation Engineering, Central South University, Changsha 410075, China;2. Joint International Research Laboratory of Key Technology for Rail Traffic Safety, Central South University, Changsha, China;3. National & Local Joint Engineering Research Center of Safety Technology for Rail Vehicle, Central South University, Changsha, China;4. State Key Laboratory of High Performance Complex Manufacturing, Central South University, Changsha, China;1. Center for Research in Molecular Medicine and Chronic Diseases (CIMUS), Health Research Institute of Santiago de Compostela (IDIS), Dept. of Pharmacology, Pharmacy and Pharmaceutical Technology, School of Pharmacy, Univ. of Santiago de Compostela, 15872 Santiago de Compostela, Spain;2. Unité Fonctionnalité et Ingénierie des Protéines (UFIP), UMR CNRS 6286, Université de Nantes, 2 rue de la Houssinière, BP92208, 44322 Nantes Cedex, France;3. Centre d''Infection et d''Immunité de Lille, Inserm U1019, CNRS UMR 8204, Université de Lille, CHU Lille, Institut Pasteur de Lille, 59000 Lille, France
Abstract:An efficient and stereoselective approach for the formal total synthesis of Stigmatellin A has been described. The key steps involved in this synthesis are desymmetrization of the bicyclic olefin to introduce two methyl and two hydroxyl chiral centers, Friedel Crafts acylation, regioselective demethylation, Baker-Venkataraman rearrangement and Grubbs cross metathesis.
Keywords:Desymmetrization  Friedel Crafts acylation  Regioselective demethylation  Baker-Venkataraman rearrangement  Cross-metathesis
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