Synthesis of (+)- and (−)-dihydropinidine by diastereoselective dimethylzinc promoted allylation of 2-methyltetrahydropyridine-N-oxide with an allylboronic ester |
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| Institution: | 1. Department of Natural Sciences, Mid Sweden University, SE-851 70 Sundsvall, Sweden;2. Chemical Ecology, Department of Crop Sciences, Swedish University of Agricultural Sciences, PO Box 44, SE-230 53 Alnarp, Sweden;1. Department of Chemistry, Indian Institute of Technology Bombay, Mumbai 400 076, India;2. Discipline of Chemistry, Indian Institute of Technology Indore, Indore 452 017, India;1. Centre of Radiochemistry and Nuclear Chemistry, Institute of Nuclear Chemistry and Technology, Warsaw, Poland;2. Department of Bioanalysis and Drug Analysis, Medicinal University of Warsaw, Warsaw, Poland;3. Department of Physicochemical Drug Analysis, Faculty of Pharmacy, Jagiellonian University Medical College, Krakow, Poland;4. Laboratory of Bioanalysis, Department of Pharmaceutical Chemistry, Drug Analyses and Radiopharmacy, Medical University, Lodz, Poland;5. Department of Pharmaceutical Chemistry, Drug Analyses and Radiopharmacy, Medical University, Lodz, Poland;6. Laboratory of Radiopharmacy, Department of Pharmaceutical Chemistry, Drug Analyses and Radiopharmacy, Medical University, Lodz, Poland;1. Departamento de Química Orgánica (Facultade de Química) e Centro Singular de Investigación en Química Biolóxica y Materiais Moleculares, Campus Vida, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain;2. Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK;1. Department of Chemistry, Faculty of Science, Tokyo University of Science, Ichigayafunagawaramachi 12, Shinjuku-ku, Tokyo 162-0826, Japan;2. Graduate School of Chemical Sciences and Technology, Tokyo University of Science, Ichigayafunagawaramachi 12, Shinjuku-ku, Tokyo 162-0826, Japan |
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| Abstract: | The enantiomers of the naturally occurring alkaloid dihydropinidine 1, potential antifeedants against the pine weevil, Hylobius abietis, were prepared by diastereoselective, dimethylzinc mediated addition of pinacolyl 2-propenylboronate 14 to nitrones (R)- and (S)-2-methyl tetrahydropyridine-N-oxide 3, prepared from d- and l-alanine, respectively. |
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