Studies toward asymmetric synthesis of leiodelide A |
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| Affiliation: | 1. Department of Chemistry, College of Life Sciences and Environment, Shanghai Normal University, 100 Guilin Road, Shanghai 200234, China;2. The Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China;1. RIKEN Center for Sustainable Resource Science, Wako, Saitama 351-0198, Japan;2. Department of Chemistry, The Graduate School of Science and Engineering, Tokyo Institute of Technology, Ookayama, Tokyo 152-8551, Japan;3. Institute for Molecular Science, Myodaiji, Okazaki 444-8787, Japan;1. Normandie Univ., COBRA, UMR 6014 et FR 3038, Univ. Rouen, INSA Rouen, CNRS, 1 rue Tesnière, 76821 Mont Saint-Aignan Cedex, France;2. Immunopathologie et Chimie Thérapeutique, Institut de Biologie Moléculaire et Cellulaire CNRS-UPR3572 et FRC 1589, 15 rue Descartes, 67084 Strasbourg Cedex, France;3. Institut Charles Gerhardt UMR 5253 CNRS-UM2-UM1-ENSCM 8, rue de l’Ecole Normale, 34296 Montpellier Cedex 5, France;1. Polymers and Functional Materials Division and Academy of Scientific & Innovative Research (AcSIR), CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 007, Telangana, India;2. Reverse Osmosis Membrane Division, CSIR-Central Salt and Marine Chemicals Research Institute, Bhavnagar 364002, Gujarat, India |
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| Abstract: | An enantioselective route for oxazoline 4, a key fragment toward the asymmetric synthesis of leiodelide A, is described. We synthesized northern subunit 6 through a Julia–Lythgoe olefination and subsequent Sharpless asymmetric dihydroxylation. Moreover, a highly diastereoselective method using well-established Evans’ asymmetric aldol condensation was developed for preparation of southern fragment 5. The additional feature of this synthetic route is the formation of oxazoline 4 through DAST-promoted cyclization of the amidation product from subunits 5 and 6. |
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| Keywords: | Natural product Macrolide Asymmetric synthesis Oxazole Leiodelide |
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