A straightforward synthesis of both enantiomers of allo-norcoronamic acids and allo-coronamic acids,by asymmetric Strecker reaction from alkylcyclopropanone acetals |
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| Institution: | 1. University of Perugia, Department of Pharmaceutical Sciences, Via Fabretti 48, 06123, Perugia, Italy;2. University of Perugia, Department of Chemistry, Biology and Biotechnology, Via Elce di Sotto 8, 06123, Perugia, Italy;3. Istituto Zooprofilattico Sperimentale dell’Umbria e delle Marche “Togo Rosati”, Via G. Salvemini 1, 06126, Perugia, Italy;1. College of Food Science and Technology, Nanjing Agricultural University, Nanjing 210095, Jiangsu, People’s Republic of China;2. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, Yunnan, People’s Republic of China;3. Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, People’s Republic of China;1. A. E. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of the Russian Academy of Sciences, 420088 Kazan, Russian Federation;2. A. M. Butlerov Institute of Chemistry, Kazan Federal University, 420008 Kazan, Russian Federation;1. Department of Biomolecular Chemistry, Faculty of Medicine, Medical University of Lodz, Mazowiecka 6/8, 92-215 Lodz, Poland;2. Institute of Biochemistry, Biological Research Centre, Hungarian Academy of Sciences, Temesvári krt. 62, Szeged H-6726, Hungary;3. Department of Medical Sciences, Section of Pharmacology and National Institute of Neuroscience, University of Ferrara, Via Fossato di Mortara 17/19, 44121 Ferrara, Italy;4. Faculty of Chemistry, University of Wroclaw, F. Joliot-Curie 14, 50-383 Wroclaw, Poland |
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| Abstract: | Methylcyclopropanone hemiacetal (2S)-3a underwent the asymmetric Strecker reaction induced by a chiral amine to provide a useful synthesis of enantiomerically pure (1R,2S)-(+)-allo-norcoronamic acid 1 in good yield and high enantiomeric excess. From racemic alkyl hemiacetal (±)-3, the same methodology also constituted a useful way to prepare both (+)-1 and (−)-1 and (+)-allo-coronamic acid 2 and its antipode (−)-2 with good yield and high enantiomeric excess. |
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