Stereoselective synthesis of biologically active tetronic acids |
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| Institution: | 1. Graduate School of Science, Osaka City University, Sumiyoshi-ku, Osaka, Japan;2. Advanced Research Institute for Natural Science and Technology, Osaka City University, Sumiyoshi-ku, Osaka, Japan;3. Research Center for Urban Health and Sports, Osaka City University, Sumiyoshi-ku, Osaka, Japan;4. Department of Environmental Science, Policy and Management, University of California, Berkeley, CA, United States;1. Cumhuriyet University, Faculty of Engineering, Chemical Engineering Department, 58140 Sivas, Turkey;2. Cumhuriyet University, Faculty of Engineering, Civil Engineering Department, 58140 Sivas, Turkey;1. Department of Surgery, Kansai Medical University, Hirakata, Osaka 573-1010, Japan;2. Division of Applied Life Sciences, Graduate School of Life and Environmental Sciences, Kyoto Prefectural University, Kyoto, Kyoto 606-8522, Japan;3. Department of Biomedical Sciences, College of Life Sciences, Ritsumeikan University, Kusatsu, Shiga 525-8577, Japan;4. Research Organization of Science and Technology, Ritsumeikan University, Kusatsu, Shiga 525-8577, Japan |
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| Abstract: | (4R)-3-Amino-4-trimethylsilyloxy-2-alkenoates (R)-3, obtained from O-trimethylsilyl protected optically active cyanohydrins (R)-1 via the Blaise reaction, are hydrolyzed under mildly acidic conditions to give optically active tetronic acids (R)-4 without racemization. From the follow-up reactions of (R)-4 investigated, only methylation with diazomethane afforded the biologically active tetronic acid derivative (R)-5a without racemization whereas acylation and reductive alkylation, respectively, resulted in partial racemization or failed on the whole. |
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