Lipase-catalyzed kinetic resolution of tetronic acid derivatives bearing a chiral quaternary carbon: total synthesis of (S)-(?)-vertinolide |
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| Institution: | 1. New Drug Research & Development Center, School of Pharmaceutical Sciences, Zhengzhou University, No. 100, KeXue DaDao, Zheng zhou, Henan Province 450001, PR China;2. School of Life Sciences, Zhengzhou University, No. 100, KeXue DaDao, Zheng zhou, Henan Province 450001, PR China;3. College of Chemistry and Molecular Engineering, Zhengzhou University, No. 100, KeXue DaDao, Zheng zhou, Henan Province 450001, PR China;1. Discovery Chemistry, Merck Research Laboratories, 2000 Galloping Hill Road, Kenilworth, NJ 07033, USA;2. Pharmaron Beijing Co., Ltd, 6 Tai-He Road, BDA, Beijing 100176, China;3. Discovery Biology, Merck Research Laboratories, 770 Sumneytown Pike, West Point, PA 19486, USA;1. School of Information Engineering, ZheJiang A&F University, Hangzhou 311300, China;2. Zhejiang Provincial Key Laboratory of Forestry Intelligent Monitoring and Information Technology, Hangzhou 311300, China;3. College of Information Science & Electronic Engineering, Zhejiang University, Hangzhou 310027, China;4. State Key Laboratory of CAD & CG, Hangzhou 310027, China;1. Faculty of Agriculture and Life Science, Hirosaki University, 3-Bunkyo-cho, Hirosaki, 036-8561, Japan;2. The United Graduate School of Agricultural Sciences, Iwate University, Morioka, 020-8550, Japan;3. Graduate School of Integrated Arts and Sciences, Hiroshima University, 1-7-1, Kagamiyama, Higashi-Hiroshima, 739-8521, Japan;4. Graduated School of Science and Technology, Hirosaki University, 3-Bunkyo-cho, Hirosaki, 036-8561, Japan;1. Program in Biotechnology, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand;2. National Center for Genetic Engineering and Biotechnology (BIOTEC), National Science and Technology Development Agency (NSTDA), 113 Thailand Science Park, Phahonyothin Road, Khlong Nueng, Khlong Luang, Pathum Thani 12120, Thailand;3. Department of Microbiology, Faculty of Science, Burapha University, Chonburi 20131, Thailand |
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| Abstract: | We have developed a chemoenzymatic synthesis of (S)-vertinolide 1 with a chiral quaternary carbon atom at C5. In the kinetic resolution of tetronic acid precursor 6, lipase PS-D furnished the recovered alcohol 6 with an (R)-stereochemistry in a ratio of 95% ee, whereas lipase AY gave (S)-alcohol 6 with 93% ee. Chemical transformations of (S)-alcohol 6 provided (S)-vertinolide 1 in 33% yield in five steps with no loss of enantiomeric excess. |
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