Asymmetric synthesis of the new marine epoxy lipid, (6S,7S,9S,10S)-6,9-epoxynonadec-18-ene-7,10-diol |
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| Institution: | 1. Department of Basic Science, Jilin Jianzhu University, Changchun 130118, PR China;2. Department of Environmental Engineering and Science, Hangzhou Dianzi University, Hangzhou 310018, PR China;3. Zhejiang Institute of Quality Inspection Science, Hangzhou 310018, PR China;4. Jilin Provincial Key Laboratory of Architectural Electricity & Comprehensive Energy Saving, School of Electrical and Electronic Information Engineering, Jilin Jianzhu University, Changchun 130118, PR China;5. Key Laboratory of Songliao Aquatic Environment, Ministry of Education, Jilin Jianzhu University, Changchun 130118, PR China |
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| Abstract: | An efficient and stereocontrolled process is described for the preparation of (6S,7S,9S,10S)-6,9-epoxynonadec-18-ene-7,10-diol, a marine epoxy lipid isolated from the brown alga, Notheia anomala. The key 2,3,5-trisubstituted tetrahydrofuran ring was constructed by stereoselective hydrogenation of the hemiketal derivative elaborated through nucleophilic addition of Grignard reagent in the presence of CeCl3 to the highly functionalized lactone derived from L-galactono-1,4-lactone. |
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