Synthesis of (−)-(5R,6S)-6-acetoxyhexadecan-5-olide by l-proline-catalyzed asymmetric aldol reactions |
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| Affiliation: | 1. National Laboratory of Applied Organic Chemistry, Institute of Organic Chemistry, Lanzhou University, Lanzhou 730000, PR China;2. Lunan Pharmaceutical Co., Ltd, Linyi, 276003, PR China;3. Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan;1. The Scientific Technological Center of Organic and Pharmaceutical Chemistry, Armenian Academy of Science, Institute of Fine Organic Chemistry of A.L.Mnjoyan, Yerevan 0014, Ave. Azatutyan 26, Armenia;2. Molecular Structure Research Center of the Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of the Republic of Armenia, Yerevan 0014, Ave. Azatutyan 26, Armenia;1. School of Pharmacy, Second Military Medical University, Shanghai 200433, China;2. Department of Chemistry, Fudan University, Shanghai 200433, China;3. State Key Lab of New Drug and Pharmaceutical Process, Shanghai Institute of Pharmaceutical Industry, Shanghai 200040, China;4. Fujian Provincial Key Laboratory of Medical Analysis, Fujian Academy of Medical Sciences, Fuzhou 350001, China;1. Chemistry Department, Faculty of Science, Kuwait University, PO Box 5969, Safat 13060, Kuwait;2. Chemistry Department, Faculty of Science, Fayoum University, Fayoum 63514, Egypt |
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| Abstract: | The natural mosquito attractant pheromone, (−)-(5R,6S)-6-acetoxyhexadecan-5-olide 1, was synthesized from readily available aldehyde 3 and cyclopentanone 4 using l-proline catalyzed asymmetric aldol reactions as the key step. |
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