The synthesis of the insect pheromone (2S,3R,7R)-3,7-dimethyltridec-2-yl acetate from racemic 3,4-dimethyl-γ-butyrolactone by diastereoselective chiral resolution |
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| Institution: | 1. Université de Rennes 1, Institut des Sciences Chimiques de Rennes, CNRS UMR 6226, Avenue du Général Leclerc, 35042 Rennes Cedex, France;2. UMR 892 INSERM/6299 CNRS/Université de Nantes, Team 8 “Cell Survival and Tumor Escape in Breast Cancer”, Institut de Recherche Thérapeutique de l''Université de Nantes, 8 quai Moncousu, BP 70721, 44007 Nantes Cedex 1, France;3. Institut de Cancérologie de l''Ouest, Centre de Lutte contre le Cancer René Gauducheau, Boulevard Jacques Monod, 44805 Saint Herblain-Nantes Cedex, France;4. Plateforme IMPACT, Biogenouest Institut de Recherche Thérapeutique de l''Université de Nantes, 8 quai Moncousu, BP 70721, 44007 Nantes Cedex 1, France;5. Bioprojet-Biotech, 4 rue du Chesnay Beauregard, BP 96205, 35762 Saint Grégoire, France;1. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China;2. College of Chemistry and Environment, Nanjing Normal University, Nanjing 210097, China;1. CNRS UPR2301, Institut de Chimie des Substances Naturelles, Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France;2. Unité Molécules de Communication et Adaptation des Microorganismes (MCAM, UMR 7245), Muséum National d''Histoire Naturelle, Sorbonne Universités, CNRS, CP52, 57 Rue Cuvier, 75005 Paris, France;3. Univ Paris-Sud, CNRS, BioCIS-UMR 8076, Chimiothérapie Antiparasitaire, LabEx LERMIT, Faculté de Pharmacie, 5 Rue J.-B. Clément, Châtenay-Malabry, F-92296, France;4. Chemical Biology and Screening Platform, National Laboratory of Biosciences, National Center for Research on Energy and Materials, Rua Giuseppe Maximo Scolfaro, 10000, Campinas, SP 13083-100, Brazil;1. Department of Chemistry and Biochemistry, University of California at Los Angeles, 607 Charles E. Young Drive East, Los Angeles, CA 90095, United States;2. Department of Biochemistry and Goodman Cancer Research Center, McGill University, Montréal, Québec, Canada |
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| Abstract: | The insect pheromone (2S,3R,7R)-3,7-dimethyltridec-2-yl acetate 1-Ac was prepared from diastereomerically enriched (2S1,3R1,7R)-1, which in turn was obtained by the coupling of racemic 3,4-dimethyl-γ-butyrolactone with (7S)-2-methyloctyllithium, followed by a Wolff–Kishner reduction of the resulting ketone. Conversion of (2S1,3R1,7R)-1 to the corresponding alkyl hydrogen phthalate and diastereomer salt formation with (S)-PhCHMeNH2 provided after several crystallizations individual diastereomer, which was later transformed into target 1-Ac after hydrolysis and acylation. |
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