Large-scale preparation of (+)-disparlure,the gypsy moth pheromone,by a practical chemico-enzymatic procedure |
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| Institution: | 1. State Key Laboratory for Structural Chemistry of Unstable and Stable Species, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China;2. University of Chinese Academy of Sciences, Beijing 100049, China;3. College of Chemistry and Material Science, The key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials, Anhui Normal University, Wuhu 241000, China;4. CAS Research/Education Center for Excellence in Molecular Sciences, Beijing 100190, China;5. Institute of Chemical Physics, School of Chemistry and Chemical Engineering, Beijing Institute of Technology, Beijing 100081, China;1. Department of Chemistry, School of Science, Alzahra University, Vanak, Tehran, Iran;2. Lecturer, Semnan University, Semnan, Iran;3. Department of Chemistry, Semnan University, Semnan, Iran |
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| Abstract: | The Sharpless asymmetric epoxidation of 8-methyl-2-nonen-1-ol performed on a large scale (over 5 moles) at room temperature gave (2S, 3R)-2, 3-epoxy-8-methyl-1-nonanol with 52%ee. The produced epoxy alcohol of low optical purity was subjected to lipase-catalyzed enatioselective acylation in order to increase the optical purity up to 85%ee. Recrystalyzation of the corresponding 3, 5-dinitrobenzoate gave optically pure epoxy alcohol. (+)-Disparlure, the gypsy moth pheromone, was synthesized in two steps from the thus obtained optically pure epoxy alcohol. |
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