Homochiral 4-hydroxy-5-hexenoic acids and their derivatives and homologues from carbohydrates |
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| Affiliation: | 1. CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China;2. Shanghai Advanced Research Institute, Chinese Academy of Sciences, 99 Haike Road, Shanghai, 201210, China;1. Department of Natural Compounds Chemistry, Faculty of Chemistry, St. Petersburg State University, Universitetskii pr. 26, Petrodvorets, 198504 St. Petersburg, Russia;2. Folkhälsan Research Center, Haartmaninkatu 8, Helsinki, 00290, Finland;3. University of Helsinki and Helsinki University Central Hospital, Heart and Lung Center, Haartmaninkatu 8, 00290 Helsinki, Finland;1. Faculty of Pharmacy, Chiba Institute of Science, 15-8 Shiomi-cho, Choshi, Chiba 288-0025, Japan;2. Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan;1. Department of Chemistry, Oakland University, 2200 N. Squirrel Road, Rochester, MI 48309-4477, USA;2. Department of Chemistry, Eastern Illinois University, 600 Lincoln Avenue, Charleston, IL 61920-3099, USA |
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| Abstract: | Efficient routes to chiral 4-hydroxy-5-hexenoic acids and lactones from d-gluconic acid-δ-lactone and l-mannonic acid-γ-lactone are described. In this approach, the starting lactones are converted to 2,6-dibromo compounds that readily undergo zinc mediated elimination to generate the terminal alkene group in concert with 2-deoxygenation. The integrity of the remaining stereocenters is preserved during the reaction. The related important pharmaceutical intermediates (S)-3-hydroxy-4-pentenoic acid and (S)-1,3-dihydroxy-4-pentene were also prepared from 2-deoxyribose via the corresponding aldonolactone. |
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