A stereoselective synthesis of (R)-5-hydroxy-3-(4-methoxyphenethyl)cyclohex-2-enone,towards total synthesis of Prelunularin |
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| Institution: | 1. Centre for Natural Products and Traditional Knowledge, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India;2. Acharya Nagarjuna University, Nagarjuna Nagar, Guntur, Andhra Pradesh 522510, India;1. Tea Research Institute, Chinese Academy of Agricultural Sciences, Hangzhou 310008, China;2. Key Laboratory of Tea Biology and Resources Utilization, Ministry of Agriculture, Hangzhou 310008, China;3. Department of Chemistry, Zhejiang University, Hangzhou 310027, China;1. Department of Chemistry, M. V. Lomonosov Moscow State University, 119991 Moscow, Russian Federation;2. A. N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, 119991 Moscow, Russian Federation;3. Plekhanov Russian University of Economics, 117997 Moscow, Russian Federation;4. Ukrainian State University of Chemical Technology, 49005 Dnipro, Ukraine;5. State Scientific Institution “Institute for Single Crystals” of National Academy of Sciences of Ukraine, 61001 Kharkiv, Ukraine |
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| Abstract: | A first chiral strategy for synthesis of (R)-5-hydroxy-3-(4-methoxyphenethyl) cyclohex-2-enone reported. Key transformation includes Barbier allylation, ionic hydrogenation, Jeffery reaction, Katsuki Sharpless asymmetric epoxidation, reductive opening of epoxide and ring closing metathesis. |
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| Keywords: | Bryophyte Prelunularin Ionic hydrogenation Ring closing metathesis |
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