Stereoselective synthesis of chiral tetrahydrofurans with potent 5-LO inhibitory activity |
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| Institution: | 1. D-211, Discovery Laboratory, Organic Chemistry Division III, Indian Institute of Chemical Technology, Hyderabad 500 007, India;2. Chorghade Enterprises, 14 Carlson Circle, Natick, MA 01760-4205, USA;3. Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK;1. WuXi AppTec (Shanghai) Co., Ltd., 288 FuTe Zhong Road, Shanghai 200131, People’s Republic of China;2. Jiangsu Kangyuan Pharmaceutical Co., Ltd., 58 Haichangnan Road, Lianyungang 222001, People’s Republic of China;1. Department of Pharmacology, Zhongshan Medical College, Sun Yat-Sen University, 74 Zhongshan Road II, Guangzhou, GD 510080, China;2. Neuroscience Institute, Morehouse School of Medicine, 720 Westview Dr SW, Atlanta, GA 30329, USA;3. School of Pharmaceutical Sciences, Sun Yat-Sen University, Guangzhou, GD 510006, China;1. Graduate School of Science and Technology, University of Toyama, Toyama 930-8555, Japan;2. Department of Hospital Pharmacy, University of Toyama, Toyama 930-0194, Japan;3. Hokuriku University, Ho-3, Kanagawa-machi, Kanazawa 920-1181, Japan;4. Kampo Research Laboratory, Kracie Pharma Ltd., Takaoka 930-0856, Toyama, Japan;5. Tokyo University of Science, Research Institute for Biomedical Science, Noda, Chiba 278-8510, Japan;6. Graduate School of Innovative Life Science, University of Toyama, 930-8555, Japan;1. Friedrich Schiller University Jena, Institute of Inorganic and Analytical Chemistry, Lessingstr. 8, 07743 Jena, Germany;2. Friedrich Schiller University Jena, Institute of Pharmacy, Philosophenweg 14, 07743 Jena, Germany;1. Department of Sciences of Life and Environment, University of Cagliari, Cittadella Universitaria, I-09042 Monserrato, CA, Italy;2. Department of Chemical and Geological Sciences, University of Cagliari, Cittadella Universitaria, I-09042 Monserrato, CA, Italy |
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| Abstract: | Chiral glyceraldehydes have been exploited for the design of convenient and scalable synthetic approaches to chiral tetrahydrofurans, which have potential as potent 5-lipoxygenase (5-LO) inhibitors. The synthesis of all four possible stereoisomers by a general methodology is reported; wherein the chirons derived from the glyceraldehyde derivatives on reaction with homopropargyl ether, cyclization and further reactions gave the targets. |
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