Stereoselective synthesis of (−)-centrolobine |
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| Institution: | 1. Department of Chemistry, Osaka University, 1–1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan;2. JST, ERATO, Lipid Active Structure Project, Osaka University, 1–1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan;3. Project Research Centre for Fundamental Science, Osaka University, 1–1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan;1. Graduate School of Infection Control Sciences, Kitasato University, 5-9-1, Shirokane, Minato-ku, Tokyo, 108-8641, Japan;2. Kitasato Institute for Life Sciences, Kitasato University, 5-9-1, Shirokane, Minato-ku, Tokyo, 108-8641, Japan;3. School of Pharmacy, Showa University, 1-5-8, Hatanodai, Shinagawa-ku, Tokyo, 142-8555, Japan;4. School of Phamaceutical Sciences, Kitasato University, 5-9-1, Shirokane, Minato-ku, Tokyo, 108-8641, Japan;1. State Key Laboratory of Environmental Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China;2. School of Chemistry and Chemical Engineering, University of Chinese Academy of Sciences, Beijing 100049, China |
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| Abstract: | The stereoselective synthesis of (−)-centrolobine has been accomplished starting from d-glyceraldehyde acetonide by a combination of chelation-controlled diastereoselective alkylation and ring-closing metathesis. A high degree of 1,3-asymmetric induction has been realized in an ether system. |
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