Transformation of (+)-thiomicamine into the p-methylthio analogue of (+)-5-epi-cytoxazone |
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| Institution: | 1. Department of Chemistry, Bard College, 30 Campus Road, Annandale-on-Hudson, NY 12504, United States;2. Department of Chemistry, Vassar College, Poughkeepsie, NY 12604, United States;1. Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang, Jiangxi 330013, PR China;2. Department of Chemistry, Nanchang University, Nanchang, Jiangxi 330031, PR China;1. Chemistry Department, College of Science, University of Anbar, Ramadi, Iraq;2. Raman Research Institute, Soft Condensed Matter Group, Sadashivanagara, Bengaluru 560080, Karnataka, India;3. Department of Chemistry, Central College Campus, Bangalore University, Bengaluru 560001, Karnataka, India;4. Liquid Crystal Research Laboratory, School of Chemical Sciences, Universiti Sains Malaysia, Minden 11800, Penang, Malaysia;1. Laboratório de Química Orgânica, Departamento de Engenharia Química and Centro de Investigação de Engenharia Química e Biotecnologia, Instituto Superior de Engenharia de Lisboa, Instituto Politécnico de Lisboa, R. Conselheiro Emídio Navarro, 1, 1959-007 Lisboa, Portugal;2. Dipartimento di Chimica e Chimica Industriale, Università di Pisa, via Risorgimento, 35, 56126 Pisa, Italy |
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| Abstract: | (2S,3S)-(+)-Thiomicamine 3, a commercially available aminodiol, was transformed into (4R,5S)-5-hydroxymethyl-4-(p-methylthiophenyl)-2-oxazolidinone 10, a compound related to cytoxazone-type biologically active natural products. The synthetic strategy of the highly regio- and stereoselective synthesis was based upon the reversal of the position of the hydroxyl and amine functionalities in 3, accomplished via azidolysis of the key intermediate, epoxide 6. |
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